Name: 57598-33-1|2-(2-Methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole|95+%
Brand: Ambeed
SKU: A529240
Price: 28.0 USD
Availability: InStock
Rating: 93 (40 reviews)

1
[ 57598-33-1 ]
[ 54646-75-2 ]
[ 96964-42-0 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium 1.) THF, 2.) THF, RT, 20 h; Yield given;
	With magnesium In tetrahydrofuran	5.a (a) To 8-phenyloctyl bromide and 21.27 mmol of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmol) in tetrahydrofuran (20 ml). After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.

Reference： [1]Perchonock; Uzinskas; McCarthy; Erhard; Gleason; Wasserman; Muccitelli; DeVan; Tucker; Vickery [Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1442 - 1452]
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5135938, 1992, A Current Patent Assignee: GLAXOSMITHKLINE PLC - US5143931, 1992, A

2
[ 57598-33-1 ]
[ 3761-92-0 ]
[ 136515-49-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; diethyl ether for 3.5h; Ambient temperature;
	In tetrahydrofuran	1.A EXAMPLE 1 A. 2-(2-n-hexylphenyl)-4,4-dimethyloxazoline. To a solution of 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (61.5g, 0.3 mmol) in 1000 ml of dry THF at 0° C. is added n-hexylmagnesiumbromide while keeping the temperature below 5° C. When the addition is finished, the reaction mixture is allowed to warm up to room temperature and stirred overnight. The reaction mixture is poured over a saturated NH4 Cl/ice mixture slowly while stirring, then extracted with ethyl acetate. The extracts are washed with water and then brine, and dried over MgSO4 to afford the subtitle compound.

Reference： [1]Nate; Sekine; Honma; Nakai; Wada; Takeda; Yabana; Nagao [Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1953 - 1968]
[2]Current Patent Assignee: ELI LILLY & CO - US5028629, 1991, A

3
[ 57598-33-1 ]
[ 15890-72-9 ]
[ 96964-41-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	In tetrahydrofuran for 20h; Ambient temperature;

Reference： [1]Perchonock; McCarthy; Erhard; Gleason; Wasserman; Muccitelli; DeVan; Tucker; Vickery; Kirchner [Journal of Medicinal Chemistry, 1985, vol. 28, # 9, p. 1145 - 1147]

4
[ 57598-33-1 ]
[ 594-19-4 ]
[ 87306-63-6 ]
4,4-dimethyl-2-(1,1-dimethylethyl)-2-(2-methoxyphenyl)oxazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	In tetrahydrofuran; pentane at -45℃; for 3h;

Reference： [1]Beak, Peter; Kerrick, Shawn T.; Gallagher, Donald J. [Journal of the American Chemical Society, 1993, vol. 115, # 23, p. 10628 - 10636]

5
[ 57598-33-1 ]
8-phenyloctylmagnesium bromide [ No CAS ]
[ 96964-42-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	In tetrahydrofuran for 20h; Ambient temperature;

Reference： [1]Perchonock; McCarthy; Erhard; Gleason; Wasserman; Muccitelli; DeVan; Tucker; Vickery; Kirchner [Journal of Medicinal Chemistry, 1985, vol. 28, # 9, p. 1145 - 1147]

6
[ 74201-13-1 ]
[ 57598-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride at 25℃; for 1h; Yield given;
	With thionyl chloride Yield given;
	With thionyl chloride In dichloromethane at 20℃;

Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / ethanol / 0.5 h / 25 °C / Inert atmosphere

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Ellefson; Prodan; Brougham; Miller [Journal of Medicinal Chemistry, 1980, vol. 23, # 9, p. 977 - 980]
[3]Location in patent: body text Ghosh, Samir; Kumar, A. Sanjeev; Soundararajan; Mehta [Synthetic Communications, 2009, vol. 39, # 21, p. 3880 - 3887]
[4]Gutierrez, David A.; Lee, Wan-Chen Cindy; Shen, Yuning; Li, Jie Jack [Tetrahedron Letters, 2016, vol. 57, # 48, p. 5372 - 5376]

7
[ 2439-77-2 ]
[ 124-68-5 ]
[ 57598-33-1 ]

Reference： [1]Heterocycles,1981,vol. 15,p. 361 - 367

8
[ 57598-33-1 ]
[ 13139-86-1 ]
[ 84392-30-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	In tetrahydrofuran Ambient temperature;

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

9
[ 57598-33-1 ]
[ 4294-57-9 ]
[ 84392-32-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 20℃; for 2h; Yield given;
	In tetrahydrofuran at 20℃; for 3h;

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: ELDRUG - EP2162441, 2016, B1 Location in patent: Paragraph 0171; 0219

10
[ 2867-59-6 ]
[ 21615-34-9 ]
[ 57598-33-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849

11
[ 57598-33-1 ]
[ 1068-55-9 ]
[ 73621-24-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	In tetrahydrofuran

Reference： [1]Palmer, Robert B.; Andersen, Niels H. [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 18, p. 2173 - 2176]

12
[ 124-68-5 ]
[ 579-75-9 ]
[ 57598-33-1 ]

Yield	Reaction Conditions	Operation in experiment
48%	With thionyl chloride
	Stage #1: 2-Methoxybenzoic acid With thionyl chloride In dichloromethane at 20℃; for 1h; Stage #2: 2-Amino-2-methyl-1-propanol In dichloromethane

Reference： [1]Palmer, Robert B.; Andersen, Niels H. [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 18, p. 2173 - 2176]
[2]Silky, Sethy; Mandal, Sudip Kumar; Ewies, Ewies Fawzy; Neerupma, Dhiman; Arun, Garg [Egyptian Journal of Chemistry, 2021, vol. 64, # 7, p. 3659 - 3664]

13
[ 57598-33-1 ]
[ 74-85-1 ]
[ 201230-82-2 ]
1-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-3-methoxyphenyl]-1-propanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In toluene at 160℃; for 20h;

Reference： [1]Le, Yutaka; Chatani, Naoto; Ogo, Takashi; Marshall, Daniel R.; Fukuyama, Takahide; Kakiuchi, Fumitoshi; Murai, Shinji [Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1475 - 1488]

14
[ 57598-33-1 ]
[ 98-81-7 ]
4,4-dimethyl-2-[2-(1-phenyl-vinyl)-phenyl]-4,5-dihydro-oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 1-bromovinylbenzene With magnesium; ethylene dibromide In tetrahydrofuran for 2h; Heating; Stage #2: 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline In tetrahydrofuran at 20℃; for 16h;

Reference： [1]Seijas, Julio A.; Vázquez-Tato, M. Pilar; Martínez, M. Montserrat; Pizzolatti, Moacir G. [Tetrahedron Letters, 2005, vol. 46, # 35, p. 5827 - 5830]

15
[ 57598-33-1 ]
[ 6502-22-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / tetrahydrofuran 2: 1.) CH₃I, 2.) NaBH₄ / 1.) EtNO₂, 2.) EtOH 3: pyridinium chlorochromate, pyridine / CH₂Cl₂
	Multi-step reaction with 4 steps 1: 98 percent 2: 94 percent / nitromethane / 70 °C 3: NaBH₄ / methanol / 1 h / 0 °C 4: HCl / tetrahydrofuran
	Multi-step reaction with 3 steps 1: 99 percent / tetrahydrofuran; diethyl ether / 3.5 h / Ambient temperature 2: 96 percent / nitromethane / 70 °C 3: 1.) NaBH₄; 2.) 5percent aq. HCl / 1.) EtOH, RT, 4 h; 2.) 65 deg C, 20 min

Reference： [1]Palmer, Robert B.; Andersen, Niels H. [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 18, p. 2173 - 2176]
[2]Wilson, Stephen R.; Mao, David T.; Khatri, Hiralal N. [Synthetic Communications, 1980, vol. 10, # 1, p. 17 - 24]
[3]Nate; Sekine; Honma; Nakai; Wada; Takeda; Yabana; Nagao [Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1953 - 1968]

16
[ 57598-33-1 ]
[ 26311-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

17
[ 57598-33-1 ]
[ 26311-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

18
[ 57598-33-1 ]
[ 100368-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

19
[ 57598-33-1 ]
[ 18110-71-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 79 percent / tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

20
[ 57598-33-1 ]
[ 39950-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 79 percent / tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

21
[ 57598-33-1 ]
[ 17103-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 79 percent / tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

22
[ 57598-33-1 ]
[ 110391-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 79 percent / tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

23
[ 57598-33-1 ]
[ 110683-66-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

24
[ 57598-33-1 ]
[ 1026061-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

25
[ 57598-33-1 ]
4'-Methoxy-3'-methyl-biphenyl-2-carboxylic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

26
[ 57598-33-1 ]
[ 1026740-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

27
[ 57598-33-1 ]
[ 1026802-35-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

28
[ 57598-33-1 ]
[ 1026471-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

29
[ 57598-33-1 ]
5-Pentyl-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature 10: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

30
[ 57598-33-1 ]
[ 1026603-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 79 percent / tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

31
[ 57598-33-1 ]
[ 1027230-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

32
[ 57598-33-1 ]
[ 1054581-75-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature 10: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

33
[ 57598-33-1 ]
[ 1026586-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

34
[ 57598-33-1 ]
[ 1026260-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

35
[ 57598-33-1 ]
[ 1026550-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

36
[ 57598-33-1 ]
[ 1026652-43-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

37
[ 57598-33-1 ]
[ 1027585-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

38
[ 57598-33-1 ]
[ 1026547-50-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

39
[ 57598-33-1 ]
2-Diphenylacetyl-5-pentyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature 10: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h 11: 1.) diisopropylethylamine / 1.) THF, 5 min, 2.) THF, RT, overnight 12: 1.0 N aq. NaOH / methanol; tetrahydrofuran / 4 h / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

40
[ 57598-33-1 ]
[ 151888-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature 10: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h 11: 1.) diisopropylethylamine / 1.) THF, 5 min, 2.) THF, RT, overnight

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

41
[ 57598-33-1 ]
2-Diphenylacetyl-5-(4-methoxy-3-methyl-phenyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature 10: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h 11: 1.) diisopropylethylamine / 1.) THF, 5 min, 2.) THF, RT, overnight 12: 1.0 N aq. NaOH / methanol; tetrahydrofuran / 4 h / Heating

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

42
[ 57598-33-1 ]
[ 1061375-01-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: tetrahydrofuran / Ambient temperature 2: H₂SO₄ / methanol / 4 h / Heating 3: 4.5 N HCl / Heating 4: H⁺ 5: LiBH₄ 6: triethylamine / CH₂Cl₂ / 1 h / 0 °C 7: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight 8: P₂O₅ / toluene / 4 h / Heating 9: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature 10: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h 11: 1.) diisopropylethylamine / 1.) THF, 5 min, 2.) THF, RT, overnight

Reference： [1]VanAtten, Mary K.; Ensinger, Carol L.; Chiu, Andrew T.; McCall, Dale E.; Nguyen, Tam T.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 3985 - 3992]

43
[ 57598-33-1 ]
4,6-dithia-5-[2-(12,12,12-trifluorododecyl)phenyl]nonanedioic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) Mg / 1.) THF, 2.) THF, RT, 20 h 2: 18 h / Heating 3: 1.) NaBH₄, 2.) 3 N HCl / 1.) MeOH, 15 min, 2.) acetone, RT, 19 h 4: BF₃*Et₂O / CH₂Cl₂ / 0.25 h

Reference： [1]Perchonock; Uzinskas; McCarthy; Erhard; Gleason; Wasserman; Muccitelli; DeVan; Tucker; Vickery [Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1442 - 1452]

44
[ 579-75-9 ]
[ 57598-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ 2: SOCl₂ 3: SOCl₂
	Multi-step reaction with 3 steps 1: 95 percent / thionyl chloride / 18 h / 20 °C 2: CH₂Cl₂ / 2 h / 20 °C 3: thionyl chloride / 1 h / 25 °C
	Multi-step reaction with 4 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.2: 3 h / 20 °C / Inert atmosphere 4.1: sodium hydroxide / ethanol / 0.5 h / 25 °C / Inert atmosphere

Reference： [1]Ellefson; Prodan; Brougham; Miller [Journal of Medicinal Chemistry, 1980, vol. 23, # 9, p. 977 - 980]
[2]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[3]Gutierrez, David A.; Lee, Wan-Chen Cindy; Shen, Yuning; Li, Jie Jack [Tetrahedron Letters, 2016, vol. 57, # 48, p. 5372 - 5376]

45
[ 21615-34-9 ]
[ 57598-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ 2: SOCl₂
	Multi-step reaction with 2 steps 1: CH₂Cl₂ / 2 h / 20 °C 2: thionyl chloride / 1 h / 25 °C
	Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / ethanol / 0.5 h / 25 °C / Inert atmosphere

Reference： [1]Ellefson; Prodan; Brougham; Miller [Journal of Medicinal Chemistry, 1980, vol. 23, # 9, p. 977 - 980]
[2]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[3]Gutierrez, David A.; Lee, Wan-Chen Cindy; Shen, Yuning; Li, Jie Jack [Tetrahedron Letters, 2016, vol. 57, # 48, p. 5372 - 5376]

46
[ 57598-33-1 ]
[ 22927-13-5 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 1953 - 1968

47
[ 57598-33-1 ]
[ 16191-28-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: 42.55 g / diisobutylaluminum hydride / toluene / 0.25 h / -78 - -70 °C 5: pyridinium chlorochromate / CH₂Cl₂ / 0.5 h / 25 °C
	Multi-step reaction with 4 steps 1: magnesium / tetrahydrofuran 2: hydrogenchloride 3: methanol 4: diisobutylaluminium hydride / methanol; water; toluene

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US5128355, 1992, A

48
[ 57598-33-1 ]
[ 7148-03-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating
	Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran 2: hydrogenchloride

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US5128355, 1992, A

49
[ 57598-33-1 ]
[ 114772-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
	Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran 2: hydrogenchloride 3: thionyl chloride / water; toluene
	Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / 2 h / 20 °C 2: trichlorophosphate; pyridine / 3 h / 100 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US5128355, 1992, A
[3]Silky, Sethy; Mandal, Sudip Kumar; Ewies, Ewies Fawzy; Neerupma, Dhiman; Arun, Garg [Egyptian Journal of Chemistry, 2021, vol. 64, # 7, p. 3659 - 3664]

50
[ 57598-33-1 ]
[ 114772-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: oxalyl chloride / CH₂Cl₂ / 3 h / 25 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

51
[ 57598-33-1 ]
[ 114772-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating
	Multi-step reaction with 4 steps 1: magnesium / tetrahydrofuran 2: hydrogenchloride 3: thionyl chloride / water; toluene 4: dibenzoyl peroxide

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US5128355, 1992, A

52
[ 57598-33-1 ]
[ 114772-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h
	Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran 2: hydrogenchloride 3: methanol

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US5128355, 1992, A

53
[ 57598-33-1 ]
[ 114772-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: oxalyl chloride / CH₂Cl₂ / 3 h / 25 °C 4: tetrahydrofuran / 1 h / 25 °C
	Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran 2: hydrogenchloride 3: tetrahydrofuran; dichloromethane; benzene

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US5128355, 1992, A

54
[ 57598-33-1 ]
[ 114772-38-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating
	Multi-step reaction with 5 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride / methanol 3: hydrogenchloride; sodium hydroxide / ethanol 4: sulfuric acid / methanol; water 5: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 5 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride / methanol 3: sodium hydroxide / methanol; dichloromethane 4: sulfuric acid / methanol; water 5: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane

	Multi-step reaction with 5 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; sodium hydrogencarbonate / methanol 3: hydrogenchloride; sodium hydroxide / ethanol 4: sulfuric acid / methanol; water 5: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 5 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; sodium hydrogencarbonate / methanol 3: sodium hydroxide / methanol; dichloromethane 4: sulfuric acid / methanol; water 5: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 5 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride / methanol 3: sodium hydroxide; sulfuric acid / water 4: sulfuric acid / methanol; water 5: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 5 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; sodium hydrogencarbonate / methanol 3: sodium hydroxide; sulfuric acid / water 4: sulfuric acid / methanol; water 5: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 6 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; potassium permanganate / pyridine; water 3: tetrahydrofuran; water 4: sodium hydroxide; sulfuric acid / water 5: sulfuric acid / methanol; water 6: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 6 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; potassium permanganate / pyridine; water 3: tetrahydrofuran; water 4: hydrogenchloride; sodium hydroxide / ethanol 5: sulfuric acid / methanol; water 6: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 6 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; potassium permanganate / pyridine; water 3: tetrahydrofuran; water 4: sodium hydroxide / methanol; dichloromethane 5: sulfuric acid / methanol; water 6: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 7 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; potassium permanganate / pyridine; water 3: thionyl chloride; sodium hydrogencarbonate / methanol; dichloromethane 4: tetrahydrofuran; water 5: sodium hydroxide / methanol; dichloromethane 6: sulfuric acid / methanol; water 7: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 7 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; potassium permanganate / pyridine; water 3: thionyl chloride; sodium hydrogencarbonate / methanol; dichloromethane 4: tetrahydrofuran; water 5: sodium hydroxide; sulfuric acid / water 6: sulfuric acid / methanol; water 7: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane
	Multi-step reaction with 7 steps 1: ammonium chloride; magnesium / tetrahydrofuran 2: hydrogenchloride; potassium permanganate / pyridine; water 3: thionyl chloride; sodium hydrogencarbonate / methanol; dichloromethane 4: tetrahydrofuran; water 5: hydrogenchloride; sodium hydroxide / ethanol 6: sulfuric acid / methanol; water 7: phosphorus tribromide; sodium hydrogencarbonate / pyridine; hexane

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[3]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[4]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[5]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[6]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[7]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[8]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[9]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[10]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[11]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[12]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[13]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A

55
[ 57598-33-1 ]
[ 114799-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 79 percent / H₂ / 10percent Pd/C / methanol / 3.5 h / 25 °C / 760 Torr 7: 69 percent / 10percent aq. NaOH / ethanol / 5 h / Heating

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

56
[ 57598-33-1 ]
[ 114772-45-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 79 percent / H₂ / 10percent Pd/C / methanol / 3.5 h / 25 °C / 760 Torr

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

57
[ 57598-33-1 ]
[ 114799-97-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr 9: 1.76 g / 0.5 N methanolic KOH / H₂O / 18 h / Heating

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

58
[ 57598-33-1 ]
[ 114772-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

59
[ 57598-33-1 ]
[ 114798-26-4 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2525 - 2547
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2525 - 2547

60
[ 57598-33-1 ]
[ 114799-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr 9: 1.76 g / 0.5 N methanolic KOH / H₂O / 18 h / Heating 10: 1.000 N aq. NaOH / tetrahydrofuran / 16 h / 25 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

61
[ 57598-33-1 ]
[ 114799-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr 9: 55 percent / CHCl₃ / 72 h / 25 °C 10: 0.5 N methanolic KOH / H₂O / 18 h / Heating

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

62
[ 57598-33-1 ]
[ 124750-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr 9: 55 percent / CHCl₃ / 72 h / 25 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

63
[ 57598-33-1 ]
[ 133909-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 4: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
	Multi-step reaction with 6 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 4: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 6: sodium borohydride / CH₂Cl₂ / 24 h / 25 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]
[2]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

64
[ 57598-33-1 ]
[ 128764-56-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr 9: 75 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, dicyclohexylcarbodiimide / 96 h / 0 °C 10: 1.68 g / anisole, trifluoroacetic acid / tetrahydrofuran; H₂O / 7 h / 25 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

65
[ 57598-33-1 ]
[ 128764-55-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr 9: 75 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, dicyclohexylcarbodiimide / 96 h / 0 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

66
[ 57598-33-1 ]
[ 128764-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 88 percent / 4.5 N aq. HCl / 12 h / Heating 3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 97 percent / thionyl chloride / CHCl₃ / 4 h / 25 °C 7: sodium azide / dimethylsulfoxide / 16 h / 25 °C 8: H₂ / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr 9: 75 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, dicyclohexylcarbodiimide / 96 h / 0 °C 10: 1.68 g / anisole, trifluoroacetic acid / tetrahydrofuran; H₂O / 7 h / 25 °C 11: 1.000 N aq. NaOH / tetrahydrofuran; methanol / 24 h / 50 °C

Reference： [1]Carini, David J.; Duncia, John V.; Aldrich, Paul E.; Chiu, Andrew T.; Johnson, Alexander L.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547]

67
[ 57598-33-1 ]
[ 23719-80-4 ]
[ 892390-50-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	In tetrahydrofuran at 0 - 20℃; for 72h;	38 To a cooled (00C) solution of 2-(2'-methoxyphenyl)-4,4-dimethyl-2-oxazoline (5.8g, 28.33mmol) in tetrahydrofuran (34ml) was added a 0.5M solution of cyclopropylmagnesium bromide in tetrahydrofuran (170ml, 85mmol). The reaction mixture was allowed to warm to room temperature and stirred for 72 hours. It was then quenched with a saturated aqueous solution of ammonium chloride (100ml), and the tetrahydrofuran was evaporated in vacuo. The residue was extracted with diethyl ether (3x100ml) and the combined organic extracts were dried over sodium sulfate, filtered and evaporated in vacuo. The crude material was purified by column chromatography using an ISCO silica cartridge eluting with a gradient of 0-20% ethyl acetate: pentane. The title compound was obtained as a white solid (4.5g, 20.9mmol, 74%). 1HNMR (400MHz, CDCI3): δ 0.67 (m, 2H), 0.96 (m, 2H), 1.41 (s, 6H), 2.63 (m, 1 H), 4.10 (s, 2H), 6.96 (d, 1 H), 7.16 (t, 1 H), 7.31 (t, 1 H), 7.65 (d, 1 H). EPO Preparation 39: 2-(2-Cyclopropylphenyl)-3,4,4-trimethyl-4,5-dihydro-1 ,3-oxazol-3-ium

Reference： [1]Current Patent Assignee: PFIZER INC - WO2006/64336, 2006, A2 Location in patent: Page/Page column 47

68
[ 57598-33-1 ]
cyclobutyl magnesium chloride [ No CAS ]
[ 892390-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 0℃;	41 The title compound was prepared as described for preparation 38, by adding cyclobutyl magnesium chloride (55mmol, 3eq.) in tetrahydrofuran (50 ml) to a solution of 2-(2-methoxyphenyl)-4,4-dimethyl-4,5- dihydro-1 ,3-oxazole (3.6Og, 18.4mmol, 1 eq.) in tetrahydrofuran (50ml) at 0°C affording, after work-up,4.27 g of the crude title compound, which was used directly in the next step.1HNMR(400MHz, CDCI3) δ: 1.4(s, 6H), 1.75-1.87(m, 1 H), 1.94-2.07(m, 1 H), 2.07-2.19(m, 2H), 2.31-2.41(m, 2H), 4.09(s, 2H), 4.12-4.2(m, 1 H), 7.17-7.23(t of m, 1 H), 7.34-7.43(m, 2H), 7.64(d, 1 H); MS APCI+ 230 [MH]+.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2006/64336, 2006, A2 Location in patent: Page/Page column 48

69
[ 57598-33-1 ]
[ 128564-66-9 ]
[ 598-30-1 ]
[ 159748-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	In cyclohexane	1 2[-5-(2-Carboxyphenyl)indol-1-yl]octanoic acid EXAMPLE 1 2[-5-(2-Carboxyphenyl)indol-1-yl]octanoic acid 5-Bromo-1-triisopropylsilylindole (25.6 mmoles, 9.0 g) was treated with sec-butyl lithium (37.8 mmoles, 27 ml of 1.4M solution in cyclohexane) and reacted with 4,4-dimethyl-2-(2-methoxy)phenyl-2-oxazoline (30.7 mmoles, 6.3 g) as in Example 2 to produce 1.72 g of 5-[2-(4,4-dimethyloxazolin-2-yl)phenyl]-1-triisopropylsilylindole. (MS)
	In cyclohexane	1 2-[5-(2-Carboxyphenyl) indol-1-yl]octanoic acid EXAMPLE 1 2-[5-(2-Carboxyphenyl) indol-1-yl]octanoic acid 5-Bromo-1-triisopropylsilylindole (25.6 mmoles, 9.0 g) was treated with sec-butyl lithium (37.8 mmoles, 27 ml of 1.4M solution in cyclohexane) and reacted with 4,4-dimethyl-2-(2-methoxy) phenyl-2-oxazoline (30.7 mmoles, 6.3 g) as in Example 2 to produce 1.72 g of 5-[2-(4,4-dimethyloxazolin-2-yl)phenyl]-1-triisopropylsilylindole. (MS)

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US5612360, 1997, A
[2]Current Patent Assignee: ELI LILLY & CO - US5556981, 1996, A

70
[ 57598-33-1 ]
[ 106-38-7 ]
[ 84392-32-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With ammonium chloride; magnesium In tetrahydrofuran	P.3 Synthesis of 4,4-dimethyl-2-(4'-methylbiphenyl-2-yl)oxazoline STR68 PREPARATIVE EXAMPLE 3 Synthesis of 4,4-dimethyl-2-(4'-methylbiphenyl-2-yl)oxazoline STR68 Tetrahydrofuran (200 ml) was added to 2.5 g (103 mmol) of flaky magnesium, followed by the addition of a small amount of dibromoethane under stirring. After the confirmation of bubbling, 13 ml (106 mmol) of 4-bromotoluene was dropwise added thereto. After the confirmation of the dissolution of the magnesium, the mixture was further stirred at room temperature for one hour. This reaction liquid was dropwise added to a solution of 10.0 g (48.7 mmol) of 4,4-dimethyl-2-(2'-methoxyphenyl)oxazoline in tetrahydrofuran (100 ml), followed by stirring for 12 hours. The reaction liquid was poured into a saturated aqueous solution of ammonium chloride, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 11.0 g of the title compound as a crystal (yield 85%). m.p.;56°-59° C. 1 H-NMR(200 MHz, CDCl3); δ (ppm) 1.30 (6H, s), 2.38 (3H, s), 3.80 (2H, s), 7.00~7.50 (7H, m), 7.70 (1H, dd, J=7.5, 1.5 Hz) FAB-MS; 266 (MH+)
	With magnesium In tetrahydrofuran	85.3 Step 3: Step 3: Preparation of 2-(4'-Methylbiphenyl-2-yl)-4,4-dimethyloxazoline 4-Methylphenyl Grignard reagent was prepared from 2.5 g of magnesium and 13 mL of 4-bromotoluene in 200 mL of anhydrous THF. The Grignard reagent was added to 10 g of the product from Step 2 in 100 mL of anhydrous THF and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue was treated with 200 mL of saturated NH4 Cl solution and the mixture was stirred at room temperature for 30 minutes. The aqueous solution was then extracted with ethyl acetate. The crude product obtained upon concentration of the ethyl acetate extracts were purified by flash column chromatography (silica gel, hexane:ethyl acetate=2:1) to give the desired compound as a colorless liquid, 11.8 g.
	With magnesium In tetrahydrofuran	85.3 Step 3: Step 3: Preparation of 2-(4'-Methylbiphenyl-2-yl)-4,4-dimethyloxazoline 4-Methylphenyl Grignard reagent was prepared from 2.5 g of magnesium and 13 mL of 4-bromotoluene in 200 mL of anhydrous THF. The Grignard reagent was added to 10 g of the product from Step 2 in 100 mL of anhydrous THF and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue was treated 200 mL of saturated NH4 Cl solution and the mixture was stirred at room temperature for 30 minutes. The aqueous solution was then extracted with ethyl acetate. The crude product obtained upon concentration of the ethyl acetate extracts were purified by flash column chromatography (silica gel, hexane: ethyl acetate=2:1) to give the desired compound as a colorless liquid, 11.8 g.

With magnesium In tetrahydrofuran at 20℃; for 2h;

Reference： [1]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US5138069, 1992, A
[3]Current Patent Assignee: DUPONT DE NEMOURS INC - US5128355, 1992, A
[4]Silky, Sethy; Mandal, Sudip Kumar; Ewies, Ewies Fawzy; Neerupma, Dhiman; Arun, Garg [Egyptian Journal of Chemistry, 2021, vol. 64, # 7, p. 3659 - 3664]

71
[ 57598-33-1 ]
[ 37796-78-4 ]
4,5-dihydro-2-[2-(6'-methylnaphth-2'-yl)-phenyl]-4,4-dimethyloxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; magnesium In tetrahydrofuran; water	14.a EXAMPLE 14 a) A solution of 4,5-dihydro-2-(2-methoxyphenyl)-4,4-dimethyloxazole (I. A. Meyers, M. A. Hanagan & A. L. Mazzu, Heterocycles 15, 361 (1981)) in 400 ml of tetrahydrofuran is added dropwise at 15° to a Grignard solution prepared from 4.69 g of magnesium and 42.59 g of 2-bromo-6-methylnaphthalene (R. G. Jones et al., J. Amer. Chem. Soc.70, 2843 (1948)) in 420 ml of tetrahydrofuran. After stirring for 4 hours at room temperature, the batch is poured onto a solution of 60 g of ammonium chloride in 1500 ml of water and extracted three times with 500 ml of ether each time. The combined ether phase is dried over MgSO4 and freed of the solvent in vacuo. Recrystallisation from hot cyclohexane yields 4,5-dihydro-2-[2-(6'-methylnaphth-2'-yl)-phenyl]-4,4-dimethyloxazole, m.p. 153°-155°.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US5506240, 1996, A

72
[ 57598-33-1 ]
4-bromobenzyl-methoxymethyl ether [ No CAS ]
[ 158144-37-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonium chloride; magnesium In tetrahydrofuran	1 Synthesis of 4,4-dimethyl-2-(4'-methoxymethoxymethylbiphenyl-2-yl)oxazoline STR69 EXAMPLE 1 Synthesis of 4,4-dimethyl-2-(4'-methoxymethoxymethylbiphenyl-2-yl)oxazoline STR69 Tetrahydrofuran (15 ml) was added to 408 mg (16.8 mmol) of flaky magnesium, followed by the addition of a small amount of dibromoethane under stirring. After the confirmation of bubbling, a solution of 3.23 g (14.0 mmol) of 4-bromobenzyl-methoxymethyl ether in tetrahydrofuran (15 ml) was dropwise added thereto. After the confirmation of the dissolution of the magnesium, the resulting mixture was further stirred at room temperature for one hour. Then, a solution of 2.10 g (10.2 mmol) of 4,4-dimethyl-2-(2'-methoxy-phenyl)oxazoline in tetrahydrofuran (15 ml) was dropwise added thereto, followed by stirring for 12 hours. The reaction liquid was poured into a saturated aqueous solution of ammonium chloride, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 3.20 g of the title compound as an oil (yield 96%). 1 H-NMR(400 MHz, CDCl3); δ (ppm) 1.30 (6H, s), 3.45(3H, s), 3.80 (2H, s), 4.64 (2H, s), 4.74 (2H, s), 7.34~7.40 (6H, m), 7.48 (1H, ddd, J=8.5, 8.0, 1.5 Hz), 7.73 (1H, dd, J=8.0, 1.5 Hz) FAB-MS; 326 (MH+)

Reference： [1]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A

73
[ 57598-33-1 ]
4-bromobenzyl-tetrahydropyranyl ether [ No CAS ]
[ 158144-38-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	With ammonium chloride; magnesium In tetrahydrofuran	2 Synthesis of 4,4-dimethyl-2-(4'-tetrahydro-pyranyloxymethylbiphenyl-2-yl)oxazoline STR70 EXAMPLE 2 Synthesis of 4,4-dimethyl-2-(4'-tetrahydro-pyranyloxymethylbiphenyl-2-yl)oxazoline STR70 Tetrahybrofuran (15 ml) was added to 1.2 g (49.4 mmol) of flaky magnesium, followed by the addition of a small amount of dibromoethane under stirring. After the confirmation of bubbling, a solution of 11.0 g (40.6 mmol) of 4-bromobenzyl-tetrahydropyranyl ether in tetrahydrofuran (15 ml) was dropwise added thereto. After the confirmation of the dissolution of the magnesium, the resulting mixture was further stirred at room temperature for one hour. Then, a solution of 7.0 g (34.1 mmol) of 4,4-dimethyl-2-(2'-methoxyphenyl)oxazoline in tetrahydrofuran (5 ml) was dropwise added thereto, followed by stirring for 12 hours. The reaction liquid was poured into a saturated aqueous solution of ammonium chloride, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 6.61 g of the title compound as an oil (yield 53%). 1 H-NMR(400 MHz, CDCl3); δ (ppm) 1.29 (6H, s), 1.50~1.94(6H, m), 3.52~3.59 (1H, m), 3.80 (2H, s), 3.91~3.97 (1H, m), 4.55 (1H, d, J=12.3 Hz), 4.73(1H, t, J=3.7 Hz), 4.84 (1H, d, J=12.3 Hz), 7.38 (4H, s), 7.34~7.40 (2H, m), 7.48(1H, ddd, J=8.0, 7.5, 1.5 Hz), 7.72 (1H, ddd, J=8.0, 1.5 1.0 Hz) FAB-MS; 366 (MH+)

Reference： [1]Current Patent Assignee: EISAI CO LTD - US5554757, 1996, A

74
[ 57598-33-1 ]
[ 15890-72-9 ]
[ 143-15-7 ]
[ 96964-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium In tetrahydrofuran; hexane; ethyl acetate	1.a (a) (a) 2-(2-Dodecylphenyl)-4,4-dimethyloxazoline To freshly prepared dodecylmagnesium bromide (from 30.13 mmoles of dodecyl bromide and 26.20 mmoles of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline [A.I. Meyers et al., J. Org. Chem., 43, 1372 (1978)](17.88 mmoles) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil. Analysis for C23 H37 NO: Calculated: C, 80.41; H, 10.85; N, 4.08. Found: C, 80.22; H, 10.56; N, 3.87.
	With magnesium In tetrahydrofuran; hexane; ethyl acetate	4.a (a) (a) 2-(2-Dodecylphenyl)-4,4-dimethyloxazoline To freshly prepared dodecylmagnesium bromide (from 30.13 mmoles of dodecyl bromide and 26.20 mmoles of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl) 4,4-dimethyloxazoline [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmoles) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil. Analysis for C23 H37 NO: Calculated: C, 80.41; H, 10.85; N, 4.08. Found: C, 80.22; H, 10.56; N, 3.87.
	With magnesium In tetrahydrofuran; hexane; ethyl acetate	1.a (a) (a) 2-(2-Dodecylphenyl)-4,4-dimethyloxazoline To freshly prepared dodecylmagnesium bromide (from 30.13 mmol of dodecyl bromide and 26.20 mmol of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmol) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil. Analysis for C23 H37 NO: Calculated: C, 80.41; H, 10.85; N, 4.08. Found: C, 80.22; H, 10.56; N, 3.87.

	With magnesium In tetrahydrofuran; hexane; ethyl acetate	1.a (a) (a) 2-(2-Dodecylphenyl)-4,4-dimethyloxazoline To freshly prepared dodecylmagnesium bromide (from 30.13 mmol of dodecyl bromide and 26.20 mmol of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmol) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford to desired product as a pale yellow oil. Analysis for C23 H37 NO: Calculated: C, 80.41; H, 10.85; N, 4.08. Found: C, 80.22; H, 10.56; N, 3.87.
	With magnesium In tetrahydrofuran; hexane; ethyl acetate	1.a (a) (a) 2-(2-Dodecylphenyl)-4,4-dimethyloxazoline To freshly prepared dodecylmagnesium bromide (from 30.13 mmoles of dodecyl bromide and 26.20 mmoles of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)) (17.88 mmoles) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil. Analysis for C23 H37 NO: Calculated: C, 80.41; H, 10.85; N, 4.08. Found: C, 80.22; H, 10.56; N, 3.87.
	With magnesium In tetrahydrofuran; hexane; ethyl acetate	1.a (a) (a) 2-(2-Dodecylphenyl)-4,4-dimethyloxazoline To freshly prepared dodecylmagnesium bromide (from 30.13 mmoles of dodecyl bromide and 26.20 mmoles of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmoles) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil. Analysis for C23 H37 NO: Calculated: C, 80.41; H, 10.85; N, 4.08. Found: C, 80.22; H, 10.56; N, 3.87.
	With magnesium In tetrahydrofuran; hexane; ethyl acetate	1.a (a) (a) 2-(2-Dodecylphenyl)-4,4-dimethyloxazoline To freshly prepared dodecylmagnesium bromide (from 30.13 mmoles of dodecyl bromide and 26.20 mmoles of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline [A. I. Myers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmoles) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil. Analysis for C23 H37 NO: Calculated: C, 80.41; H, 10.85; N, 4.08. Found: C, 80.22; H, 10.56; N, 3.87.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4937253, 1990, A
[2]Current Patent Assignee: SWEDISH MATCH AB; GLAXOSMITHKLINE PLC - US4954513, 1990, A
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5135938, 1992, A
[4]Current Patent Assignee: GLAXOSMITHKLINE PLC - US5143931, 1992, A
[5]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4820719, 1989, A
[6]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4871771, 1989, A Current Patent Assignee: GLAXOSMITHKLINE PLC - US4730005, 1988, A
[7]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4874792, 1989, A

75
[ 57598-33-1 ]
[ 54646-75-2 ]
8-phenyloctylmagnesium bromide [ No CAS ]
[ 96964-42-0 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium In tetrahydrofuran	7.a (a) Following the procedures of Example 1(a), (b) and (c), to 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) in tetrahydrofuran (20 ml). After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.
	With magnesium In tetrahydrofuran	1.a (a) To 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] in tetrahydrofuran (20 ml). After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.
	With magnesium In tetrahydrofuran	7.a (a) (a) 2-(8-Phenyloctyl)benzaldehyde Following the procedures of Example 1(a), (b) and (c), to 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) in tetrahydrofuran (20 ml). [The 8-phenyloctyl bromide was prepared from 8-phenyloctanol, carbon tetrabromide and triphenylphosphine in methylene chloride as described in Example 6(a).] After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.

	With magnesium In tetrahydrofuran	7.a (a) (a) 2-(8-Phenyloctyl)benzaldehyde Following the procedures of Example 1(a), (b) and (c), to 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) in tetrahydrofuran (20 ml). (The 8-phenyloctyl bromide was prepared from 8-phenyloctanol, carbon tetrabromide and triphenylphosphine in methylene chloride analogous to the procedure described in Example 22(a).) After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.
	With magnesium In tetrahydrofuran	6.a (a) (a) 2-(8-Phenyloctyl)benzaldehyde Following the procedures of Example 1(a), (b) and (c), to 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) in tetrahydrofuran (20 ml). [The 8-phenyloctyl bromide was prepared from 8-phenyloctanol, carbon tetrabromide and triphenylphosphine in methylene chloride as described in Example 5(a).] After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.
	With magnesium In tetrahydrofuran	7.a (a) (a) 2-(8-Phenyloctyl)benzaldehyde Following the procedures of Example 1(a), (b) and (c), to 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) in tetrahydrofuran (20 ml). [The 8-phenyloctyl bromide was prepared from 8-phenyloctanol, carbon tetrabromide and triphenylphosphine in methylene chloride analogous to the procedure described in Example 22(a).] After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.
	With magnesium In tetrahydrofuran	1.a (a) To 8-phenyloctylmagnesium bromide (from 24.25 mmol of 8-phenyloctyl bromide and 21.27 mmol of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmol) [A.I. Meyers et al., J. Org. Chem. , 43 , 1372 (1978)] in tetrahydrofuran (20 ml). After stirring for 24 hours, the reaction mixture was worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.
	With magnesium In tetrahydrofuran	1.a (a) To 8-phenyloctylmagnesium bromide (from 24.25 mmol of 8-phenyloctyl bromide and 21.27 mmol of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4, 4-dimethyloxazoline (17.10 mmol) [A.I. Meyers et al., J. Org. Chem., 43 , 1372 (1978)] in tetrahydrofuran (20 ml). After stirring for 24 hours, the reaction mixture was worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4937253, 1990, A
[2]Current Patent Assignee: SWEDISH MATCH AB; GLAXOSMITHKLINE PLC - US4954513, 1990, A
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4730005, 1988, A
[4]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4820719, 1989, A
[5]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4871771, 1989, A
[6]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4874792, 1989, A
[7]Current Patent Assignee: GLAXOSMITHKLINE PLC - EP313697, 1989, A1
[8]Current Patent Assignee: GLAXOSMITHKLINE PLC - EP296732, 1991, B1

76
[ 57598-33-1 ]
[ 578-57-4 ]
[ 16750-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; magnesium In tetrahydrofuran	17.A Step A. Step A. Preparation of 2-(2'-Methoxy-[1,1'-biphenyl]-2-yl)-4,4-dimethyl-2-oxazoline 2-Methoxyphenylmagnesium bromide, prepared from 2-bromoanisole (22.4 g, 120 mmol) and magnesium (2.9 g, 120 mmol), in dry THF (75 ml) was added dropwise to a stirred solution of 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (20.4 g, 100 mmol) in dry THF (150 ml) under N2 at 20° C. Stirring of the solution was continued for 20 hours and then the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The resulting mixture was extracted with ether (2*500 ml), dried over MgSO4, filtered and evaporated.
	With ammonium chloride; magnesium In tetrahydrofuran	17.A Step A. Step A. Preparation of 2-(2'-Methoxy-[1,1'-biphenyl]-2-yl)-4,4-dimethyl-2-oxazoline. 2-Methoxyphenylmagnesium bromide, prepared from 2-bromoanisole (22.4 g, 120 mmol) and magnesium (2.9 g, 120 mmol), in dry THF (75 ml) was added dropwise to a stirred solution of 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (20.4 g, 100 mmol) in dry THF (150 ml) under N2 at 20° C. Stirring of the solution was continued for 20 hours and then the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The resulting mixture was extracted with ether (2*500 ml), dried over MgSO4, filtered and evaporated.
	With ammonium chloride; magnesium In tetrahydrofuran	17.A Preparation of (E)-6-[2-(2'-methoxy-[1,1'-biphenyl]-2-yl)ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one. Step A. Preparation of 2-(2'-Methoxy-[1,1'-biphenyl]-2-yl)-4,4-dimethyl-2-oxazoline. 2-Methoxyphenylmagnesium bromide, prepared from 2-bromoanisole (22.4 g, 120 mmol) and magnesium (2.9 g, 120 mmol), in dry THF (75 ml) was added dropwise to a stirred solution of 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (20.4 g, 100 mmol) in dry THF (150 ml) under N2 at 20° C. Stirring of the solution was continued for 20 hours and then the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The resulting mixture was extracted with ether (2*500 ml), dried over MgSO4, filtered and evaporated.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US4567289, 1986, A
[2]Current Patent Assignee: MERCK & CO INC - US4375475, 1983, A
[3]Current Patent Assignee: MERCK & CO INC - US4459422, 1984, A

77
[ 57598-33-1 ]
[ 60-29-7 ]
[ 557-91-5 ]
[ 92-66-0 ]
[ 84392-22-3 ]

Yield	Reaction Conditions	Operation in experiment
16%	With magnesium In tetrahydrofuran; dichloromethane	3.a a. a. Preparation of 2-(4,4-Dimethyl-2-oxazolin-2-yl)-4'-phenylbiphenyl A mechanically stirred solution of magnesium turnings (Mallinckrodt, for Grignards reaction, 2.95 g, 0.12 mole) and 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (23.4 g, 0.114 mole) in 100 mL dry tetrahydrofuran under nitrogen was prepared. To this was added a crystal of iodine, 1 mL of dibromoethane and 2 mL of neat p-bromophenylbenzene (also known as p-bromobiphenyl) to initiate the Grignard reaction. Following initiation of the reaction, the remainder of the p-bromophenylbenzene (28 g, 0.12 mole total) in 100 mL dry tetrahydrofuran was added dropwise at a rate sufficient to maintain the reaction of gentle reflux. The addition took 1 hr, at the end of which the reaction was heated to reflux for 4 hr and then allowed to stir overnight at room temperature. The reaction was then worked up by adding 15 mL water to the stirred mixture to coagulate the salts. The tetrahydrofuran was decanted and the remaining solids were slurried twice with 300 mL ethyl ether and twice with 300 mL dichloromethane. Each organic extract was decanted from the solids in turn and combined and evaporated under reduced pressure to an oil. The oil was redissolved in 300 mL dichloromethane, washed once with 100 mL water and once with 100 mL saturated chloride solution, dried and concentrated under reduced pressure to an oil. The oil was chromatographed, eluding with ethyl acetate/petroleum ether to yield a solid. Recrystallization from acetone/petroleum ether afforded 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-phenyl-biphenyl (16% yield, m.p. 95°-97°).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4578522, 1986, A

78
[ 57598-33-1 ]
[ 60-29-7 ]
[ 557-91-5 ]
[ 402-43-7 ]
[ 84392-18-7 ]

Yield	Reaction Conditions	Operation in experiment
33%	With magnesium In tetrahydrofuran; dichloromethane; water	1.a a. a. Preparation of 2-(4,4-Dimethyl-2-oxazolin-2-yl)-4'-trifluoromethylbiphenyl A mechanically stirred solution of magnesium turnings (5.1 g, 0.21 mole) Mallinckrodt, for Grignards reaction, and 2-(2-methoxyphenyl)-4,4dimethyl-2-oxazoline (41 g, 0.2 mole) in 50 mL dry tetrahydrofuran under nitrogen was prepared. To this was added a crystal of iodine, 1 mL of dibromethane and 2 mL of neat p-bromo trifluoromethylbenzene to initiate the Grignard reaction. Following initiation of the reaction, the remainder of the p-bromotrifluoromethylbenzene (50 g, 0.22 mole total) in 100 mL dry tetrahydrofuran was added dropwise at a rate sufficient to maintain the reaction at gentle reflux. The addition took 1 hr. At the end of the addition period, the reaction mixture was heated to reflux for 3 hr. The reaction mixture was then cooled to room temperature and 10 mL water was added dropwise to coagulate the salts. The tetrahydrofuran was decanted and the remaining solids were slurried twice with 300 mL ethyl ether and twice with 300 mL dichloromethane. Each organic extract was decanted from the solids in turn and combined and evaporated under reduced pressure to an oil. This oil was redissolved in 300 mL dichloromethane, washed once with 100 mL water and once with 10 mL saturated sodium chloride solution, dried and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (0.040 mm, 95°) to yield 2-(4,4-dimethyl-2-oxazoline-2-yl)-4'-trifluoromethylbiphenyl, yield 33%. A sample was recrystallized from 30°-60° petroleum ether (mp 50°-51°). Elemental Analysis: Calculated for C18 H16 F3 NO: C, 67.70; H, 5.05; N, 4.39. Found: C, 67.62; H, 5.09; N, 4.39.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4578522, 1986, A

79
[ 57598-33-1 ]
p-iodo-n-butylbenzene [ No CAS ]
[ 60-29-7 ]
[ 557-91-5 ]
[ 20651-67-6 ]
[ 84392-20-1 ]

Yield	Reaction Conditions	Operation in experiment
25%	With magnesium; In tetrahydrofuran; dichloromethane; water;	a. Preparation of 2-(4,4-Dimethyl-2-oxazolin-2-yl)-4'-n-butylbiphenyl A mechanically stirred solution of magnesium turnings (Mallinckrodt, for Grignard's reaction, 3.75 g., 0.154 mole) and 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (30 g, 0.146 mole) in 50 mL dry tetrahydrofuran under nitrogen was prepared. To this was added a crystal of iodine, 1 mL of dibromoethane and 2 mL of neat p-Iodo n-butylbenzene to initiate the Grignard reaction. After warming to initiate the reaction, the remainder of the p-iodo-n-butylbenzene (40 g, 0.154 mole) in 50 mL dry tetrahydrofuran was added dropwise at a rate sufficient to maintain the reaction at gentle reflux. The addition took 1 hr and the reaction mixture was then heated at reflux for 3 hr. The reaction was then cooled to room temperature and 15 mL water was added dropwise to coagulate the salts. The tetrahydrofuran was decanted and the remaining solids were slurried twice with 200 mL ethyl ether and twice with 300 mL dichloromethane. Each organic extract was decanted from the solids in turn and combined and evaporated under reduced pressure to an oil. The oil was redissolved in 300 mL dichloromethane, washed once with 100 ml saturated sodium chloride solution, dried and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (0.027 Torr, 130) to yield 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-n-butylbiphenyl as an oil, yield 25%.

Reference： [1]Patent: US4578522,1986,A

80
[ 57598-33-1 ]
12,12,12-trifluorododecylmagnesium bromide [ No CAS ]
[ 102684-53-7 ]
[ 127948-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium In tetrahydrofuran	8.a (a) (a) 2-(12,12,12-Trifluorododecyl)benzaldehyde Following the procedures of Example 1(a), (b) and (c), 12,12,12-trifluorododecylmagnesium bromide (from 29.19 mmoles of 12,12,12-trifluorododecyl bromide and 25.71 mmoles of magnesium) was reacted with 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (20.17 mmoles) in tetrahydrofuran to give 2-[2-(12,12,12-trifluorododecyl)phenyl]-4,4-dimethyloxazoline.
	With magnesium In tetrahydrofuran	7.a (a) (a) 2-(12,12,12-trifluorododecyl)benzaldehyde Following the procedures of Example 1(a), (b) and (c), 12,12,12-trifluorododecylmagnesium bromide (from 29.19 mmoles of 12,12,12-trifluorododecyl bromide and 25.71 mmoles of magnesium) was reacted with 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (20.17 mmoles) in tetrahydrofuran to give 2-[2-(12,12,12-trifluorododecyl)phenyl]-4,4-dimethyloxazoline.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4730005, 1988, A
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4871771, 1989, A

81
[ 57598-33-1 ]
4-(4-butylphenyl)butylmagnesium bromide [ No CAS ]
[ 102684-56-0 ]
[ 127948-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium In tetrahydrofuran	11.a (a) Following the procedures of Example 1(a), (b) and (c), to 4-(4-butylphenyl)butylmagnesium bromide (from 21.47 mmoles of 4-(4-butylphenyl)butyl bromide and 18.96 mmoles of magnesium) in distilled tetrahydrofuran (35 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (16.32 mmoles) in tetrahydrofuran (15 ml). Workup of the reaction mixture furnished 2-[2-(4-(4-butylphenyl)butyl)phenyl]-4,4-dimethyloxazoline as an oil.
	With magnesium In tetrahydrofuran	9.a (a) Following the procedures of Example 1(a), (b) and (c), to 4-(4-butylphenyl)butylmagnesium bromide (from 21.47 mmoles of 4-(4-butylphenyl)butyl bromide and 18.96 mmoles of magnesium) in distilled tetrahydrofuran (35 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (16.32 mmoles) in tetrahydrofuran (15 ml). Workup of the reaction mixture furnished 2-[2-(4-(4-butylphenyl)butyl)phenyl]-4,4-dimethyloxazoline as an oil.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4730005, 1988, A
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4871771, 1989, A

82
[ 57598-33-1 ]
[ 24856-58-4 ]
[ 1191259-50-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 70℃; for 2.5h; Reflux; Inert atmosphere; Stage #2: 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline In tetrahydrofuran at 56℃; for 16h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 5℃;

Reference： [1]Location in patent: experimental part Ghosh, Samir; Kumar, A. Sanjeev; Soundararajan; Mehta [Synthetic Communications, 2009, vol. 39, # 21, p. 3880 - 3887]

83
[ 57598-33-1 ]
[ 112484-85-2 ]
[ 1420880-35-8 ]

Yield	Reaction Conditions	Operation in experiment
78.6%	Stage #1: 2,3,5,6-tetra-[²H]-4-bromo toluene With iodine; magnesium In tetrahydrofuran at 20 - 50℃; for 2.5h; Stage #2: 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline In tetrahydrofuran at 20℃; for 8h;

Reference： [1]Zhang, Chi; Shen, Zucheng; Tian, Lei; Chen, Liqin [Journal of labelled compounds and radiopharmaceuticals, 2012, vol. 55, # 11, p. 401 - 405]

84
[ 57598-33-1 ]
2-(2-fluoro-6-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With palladium (II) nitrate; silver nitrate; N-fluorobis(benzenesulfon)imide In acetonitrile at 80℃; for 24h; Inert atmosphere; Microwave irradiation; Sealed tube;	General Procedures for Fluorination General procedure: As a typical experiment, the oxazoline derivative 5 (0.5 mmol), NFSI (0.75mmol), Pd(NO3)2 (0.1 mmol), and AgNO3 (0.25mmol) were charged into an oven dried microwave reaction vial, equipped with a magnetic stirring bar and sealed. The reaction vial was evacuated and purged several times with nitrogen. Anhydrous acetonitrile (5 mL) was added, and the microwave vial purged several times with nitrogen. The microwave vial was placed in a heating block at 80 °C and reactants were allowed to stir for 24hr. After cooling to room temperature, the reaction mixture was filtered through a plug of silica, using ethyl acetate and then washed twice with 3% triethylamine in water solution, twice with brine and then the organic layerwas dried over MgSO4 and filtered. The organic layer was concentrated in vacuo and the residue and was analyzed by gas chromatography using dodecane as an internal standardto determine the conversion of the fluorinated product. The crude product was purified by silica gel column chromatography using an appropriate ratio of the eluent.

Reference： [1]Gutierrez, David A.; Lee, Wan-Chen Cindy; Shen, Yuning; Li, Jie Jack [Tetrahedron Letters, 2016, vol. 57, # 48, p. 5372 - 5376]

85
C₁₃H₁₉NO₅S [ No CAS ]
[ 57598-33-1 ]

Yield	Reaction Conditions	Operation in experiment
0.861 g	With sodium hydroxide In ethanol at 25℃; for 0.5h; Inert atmosphere;	General Procedures for Preparations of Aryl-2-oxazolines General procedure: Aryl acid (10 mmol) was dissolved in 20 mL of dried methylene chloride and cooled to 0 °C; 5 drops of DMF was added to the suspension. Oxalyl chloride (12 mmol) was added drop-wise to the reaction mixture. The reaction was warmed to room temperature and stirred for 3 h. The solvent was removed in vacuo and the residue was dried for 1 h on high vacuum. The residue was dissolved in 15 mL of methylene chloride and added drop wise to a suspension of 2-amino-2-methyl-1-propanol (1.39 g, 12 mmol), triethylamine (2.02 g, 20 mmol) in 35 mL of methylene chloride at 0 oC. The reaction stirred for 3 hand was warmed to rt. The reaction was diluted with methylene chloride and washed once with dilute HCl and washed twice with brine. The organic layer was dried, (MgSO4) filtered, and concentrated in vacuo to give the crude amide intermediate. The crude amide intermediate (2.07 g 10 mmol) was dissolved in 50 mL of DCM and triethylamine(1.21 g, 12 mmol) was added. The reaction was stirred for 30 min at 0 oC. Mesyl chloride (1.37 g, 12 mmol) was added drop wise and the reaction warmed to room temperature and stirred for 3 h. The reaction was diluted with DCM and washed twice with dilute HCl and twice with brine. The organic layer was dried,(MgSO4), filtered, and concentrated in vacuo to give the crude mesylate intermediate. The crude mesylate product was purified via flash chromatography in a gradient of hexane ethyl acetate respectively. The purified product was then diluted in 20 mL of ethanol and sodium hydroxide (480 mg, 9.3 mmol) was added and the reaction was stirred for 30 min. The reaction mixture was diluted with ethyl acetate and washed 3 times with brine. The organic layer was dried over MgSO4 filtered and concentrated in vacuo to afford the product after flash chromatography.

Reference： [1]Gutierrez, David A.; Lee, Wan-Chen Cindy; Shen, Yuning; Li, Jie Jack [Tetrahedron Letters, 2016, vol. 57, # 48, p. 5372 - 5376]

86
[ 57598-33-1 ]
[ 103-67-3 ]
N-benzyl-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-N-methylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: benzyl-methyl-amine With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline In tetrahydrofuran; hexane at 20℃; for 18h; Inert atmosphere;	N-Benzyl-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-N-methylaniline 21 A literature procedure14 was adapted as follows: under a nitrogen atmosphere, n-butyllithium (2.5 M in hexane, 4.0 mL, 10.0 mmol) was addeddropwise to a stirred -78 °C solution of N-benzylmethylamine (1.3 mL, 1.22 g, 10.1 mmol) in dry THF (15 mL). Once the addition wascomplete, the reaction mixture was allowed to warm to 0 °C for 30 min before a solution of 2-(2-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole15 (2.06 g, 10.0 mmol) in dry THF (20 mL) was added dropwise. The reaction mixture was allowed to warm to rt over 18 hbefore being quenched by addition of water (4 mL) and concentrated at reduced pressure. The residue was partitioned between Et2O (100 mL)and water (100 mL), the two layers were separated and the aqueous layer re-extracted with Et2O (2 × 50 mL). The combined organic layers werewashed with sat aq. Na2CO3 (100 mL) before being dried and evaporated. The crude residue was purified by column chromatography (SiO2,Et2O/hexane 7:3) to give, at Rf 0.35, 21 (1.60 g, 54%) as a yellow oil. IR: 2965, 1646, 1598, 1495, 1452, 1364, 1310, 1100, 1037, 965, 871, 758,699 cm-1. 1H NMR (500 MHz): δ = 7.61 (dd, J = 7.5, 1.5 Hz, 1 H), 7.33-7.28 (m, 5 H), 7.26-7.22 (m, 1 H), 6.95 (d, J = 8.5 Hz, 1 H), 6.92 (t, J= 7.5 Hz, 1 H), 4.30 (s, 2 H, CH2), 3.98 (s, 2 H, CH2), 2.74 (s, 3 H, NCH3), 1.31 (s, 6 H, CH3). 13C NMR (75 MHz): δ = 164.0 (C=N), 151.5 (C),138.2 (C), 132.0 (CH), 131.2 (CH), 128.2 (2 CH), 127.8 (2 CH), 126.9 (CH), 120.3 (C), 120.1 (CH), 118.2 (CH), 79.1 (OCH2), 67.0 (C), 60.1(NCH2), 39.7 (NCH3), 28.3 (CH3). HRMS (ESI+): m/z calcd for C19H23N2O [M+H]+: 295.1805; found: 295.1796.

Reference： [1]Aitken, R. Alan; Harper, Andrew D; Slawin, Alexandra M. Z. [Synlett, 2017, vol. 28, # 14, p. 1738 - 1742]

87
[ 57598-33-1 ]
[ 931-51-1 ]
2-(2-cyclohexylphenyl)-4,4-dimethyl-4,5-dihydrooxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran; diethyl ether at 25℃; for 1h; Inert atmosphere;

Reference： [1]Hess; Guelen; Alandini; Mourati; Guersoy; Knochel [Chemistry - A European Journal, 2022, vol. 28, # 1]

88
[ 57598-33-1 ]
((2S)-bicyclo[2.2.1]heptan-2-yl)magnesium bromide [ No CAS ]
2-(2-((2S)-bicyclo[2.2.1]heptan-2-yl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;

Reference： [1]Hess; Guelen; Alandini; Mourati; Guersoy; Knochel [Chemistry - A European Journal, 2022, vol. 28, # 1]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	57598-33-1	MDL No. :	MFCD00151837
Formula :	C₁₂H₁₅NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZGDUNGBWVZKWGE-UHFFFAOYSA-N
M.W :	205.25	Pubchem ID :	333189
Synonyms :

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	63.15
TPSA :	30.82 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Log Po/w (iLOGP) :	2.73
Log Po/w (XLOGP3) :	2.02
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	2.12
Log Po/w (SILICOS-IT) :	3.43
Consensus Log Po/w :	2.43

[ CAS No. 57598-33-1 ] {[proInfo.proName]}

Quality Control of [ 57598-33-1 ]

Related Doc. of [ 57598-33-1 ]

Product Details of [ 57598-33-1 ]

Calculated chemistry of [ 57598-33-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 57598-33-1 ]

Application In Synthesis of [ 57598-33-1 ]

[ 57598-33-1 ] Synthesis Path-Upstream 1~3

[ 57598-33-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 57598-33-1 ]

Aryls

Ethers

Related Parent Nucleus of
[ 57598-33-1 ]

Oxazolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.55
Solubility :	0.58 mg/ml ; 0.00282 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	1.04 mg/ml ; 0.00507 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.9
Solubility :	0.026 mg/ml ; 0.000126 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.85

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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Code	Phrase
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P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 57598-33-1 ] {[proInfo.proName]}

Quality Control of [ 57598-33-1 ]

Related Doc. of [ 57598-33-1 ]

Product Details of [ 57598-33-1 ]

Calculated chemistry of [ 57598-33-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 57598-33-1 ]

Application In Synthesis of [ 57598-33-1 ]

[ 57598-33-1 ] Synthesis Path-Upstream 1~3

[ 57598-33-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 57598-33-1 ]

Aryls

Ethers

Related Parent Nucleus of [ 57598-33-1 ]

Oxazolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 57598-33-1 ]

Related Parent Nucleus of
[ 57598-33-1 ]