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Chemical Structure| 40877-19-8
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Product Details of [ 40877-19-8 ]

CAS No. :40877-19-8 MDL No. :MFCD00018995
Formula : C11H13ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :212.67 Pubchem ID :-
Synonyms :

Safety of [ 40877-19-8 ]

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

Application In Synthesis of [ 40877-19-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 40877-19-8 ]

[ 40877-19-8 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 100-66-3 ]
  • [ 4635-59-0 ]
  • [ 40877-19-8 ]
YieldReaction ConditionsOperation in experiment
99% With aluminum (III) chloride In dichloromethane at 0 - 15℃; for 1h; 1.1-19.1 Step (1) Synthesis of γ-chloro-4-methoxyphenylbutanone 2 Add anisole 1 (1.93g, 17.87mmol), anhydrous aluminum chloride (1.55g, 11.62mmol), 3mL of dry dichloromethane into a three-necked flask, slowly add 4-chlorobutyryl chloride dropwise at 0°C (1.26g, 8.94mmol), remove the ice-water bath after the addition is complete, stir the reaction at 15°C for 1h, and then add ice water to quench it, extract with dichloromethane, and wash the organic layer with water. Dry with anhydrous sodium sulfate, filter, concentrate, separate by column chromatography (petroleum ether/ethyl acetate=125/1), and spin dry. The product γ-chloro-4-methoxyphenylbutanone 2 (white crystal) was obtained with a yield of 99%.
99% With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 1h; Preparation of 4-chloro-1-(4-methoxyphenyl)-1-butanone (14) Anisole (13, 1.93 g, 17.87 mmol, 2.0 equiv), aluminum chloride (1.55 g, 11.62 mmol, 1.3 equiv) and dry dichloromethane (3 mL) was taken in a round bottom flask. The solution was cooled to 0 °C and 4-chlorobutyryl chloride (1.0 mL, 8.94 mmol, 1.0 equiv) was added dropwise at ice cooled condition. The resulting suspension was stirred at room temperature for 1 h. The reaction was quenched by pouring the orange colored solution into an ice/water mixture. Dichloromethane was used to extract the desired product, and the organic layer was washed with water, dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=125/1) to give compound 14 as a white solid (1.88 g, 99%). Mp 31.7-32.7 °C. 1H NMR (600 MHz, DMSO-d6) δ 7.94 (d, J = 8.9 Hz, 2H), 7.04 (d, J = 8.9 Hz, 2H), 3.84 (s, 3H), 3.70 (t, J = 6.7 Hz, 2H), 3.11 (t, J = 7.1 Hz, 2H), 2.05 (quin, J = 6.9 Hz, 2H). 13C NMR (151 MHz, DMSO-d6) δ 197.72, 163.59, 130.68, 129.87, 114.28, 56.18, 45.39, 35.19, 27.47. HRMS (ESI): m/z [M+H]+ calcd for C11H14ClO2: 213.0677; found: 213.0679.
97% Stage #1: methoxybenzene With aluminum (III) chloride In toluene at -10℃; for 0.25h; Stage #2: 4-Chlorobutanoyl chloride In toluene at -10℃; for 0.75h; 1 To a cooled solution of 10.8 g (0.1 mol) anisole in 100 ml anhydrous toluene 13.3 g (0.1 mol) aluminium trichloride was added in portions over 15 minutes at -100C then 15.5 g (12.3 ml, 0.1 mmol) 4-chloro-butyryl chloride were added over 15 EPO minutes keeping the temperature at -100C. After stirring for additional 30 minutes at -1O0C the reaction mixture was hydrolyzed and the layers were separated. The aqueous layer was extracted with toluene (three times 100 ml) and the combined organic layers were dried and evaporated to yield 20.8 g (97%) 4-chloro-l-(4- methoxy-phenyl)-butan-l-one as a light beige liquid that solidified on standing.The product was used without further purification.1H-NMR (400 MHEz, Dg-DMSO): δ= 2.06 (quintet, 2H); 3.12 (t, 2H); 3.71 (t, 2H); 3.85 (s, 3H); 7.05 (d, 2H); 7.95 (d, 2H).
95% In carbon disulfide at 40 - 50℃; for 0.5h; reactions with var. aromatic compounds;
95% In carbon disulfide at 40 - 50℃; for 0.5h;
90% With aluminum (III) chloride In dichloromethane at 5 - 15℃; for 2h; 44 4-Chloro-4'-methoxybutyrophenone. To a stirred, ice cooled solution of anisole (5.41 g, 50 mmol) and 4-chlorobutyryl chloride (7.8 g, 55 mmol) in dry DCM (200 mL) anhydrous AlCl3 (7.60 g, 57 mmol) was added within 1 h maintaining the temperature below 5°C. The mixture was allowed to warm to 15°C (2 h), and then was poured on ice (300 g). Conc. HCl (10 mL) was added, the organic layer was separated, washed with 5% NaHCO3 (200 mL),dried over CaCl2, and evaporated. The residue was purified by column chromatography in toluene to give the desired ketone as a colourless oil which solidifies on storage (9.55g, 90%).
89% Stage #1: 4-Chlorobutanoyl chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: methoxybenzene In 1,2-dichloro-ethane at -15℃; for 1h; Inert atmosphere;
56.4% With aluminium trichloride In carbon disulfide at 20℃; for 2h;
With aluminium trichloride In 1,2-dichloro-ethane for 0.5h; Ambient temperature;
With aluminium trichloride
With aluminum (III) chloride In dichloromethane at 0 - 20℃;
With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 3h; Inert atmosphere; Generalprocedure for the synthesis of γ-chlorobutyrophenone (7a-e) General procedure: 4-Chlorobutyryl chloride (2.5 mL, 21.25 mmol, 1.0 equiv), benzene (10 mL, 106.25 mmol, 5.0 equiv) and dry dichloromethane (30 mL) was taken in a round bottom flask under nitrogen atmosphere. The solution was cooled to 0 C and aluminum chloride(3.3 g) was added portion wise at ice cooled condition. The resulting suspension was stirred for 3 h at 25 C. The reaction was quenched by pouring the orange colored solution into an ice/water mixture. Dichloromethane was used to extract the desired product, and the organic layer was washed with brine (10 mL), dried withNa2SO4, and concentrated in vacuo. The desired product (7a) was purified via column chromatography using eluent pet ether-ethyl acetate (98:2). Similar procedure was followed for the synthesis of substituted c-chlorobutyrophenones (7b-e).
With aluminum (III) chloride at 0 - 20℃; for 2.08333h; General procedure: Anhydrous aluminum trichloride (3 g, 22 mmol) was added in portions under stirring to a solution of ω-chlorocarboxylic acid chloride (20 mmol) and aromatic hydrocarbon (25 mmol) in a solvent (an excess of the same aromatic hydrocarbon or methylene chloride, 10 mL) cooled to 0 °C for 5 min, and the resulting solution was stirred for 1 h at 0 °C and then 1 h at 20 °C. The mixture was poured onto ice (20 g), the organic layer was separated, and the aqueous layer was extracted with methylene chloride (3 × 30 mL). The extracts were united, dried with anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by column chromatography (l = 5 cm, d = 5 cm) on silica gel eluting with methylene chloride. The chromatographically homogeneous product was used without further purification for the synthesis of alkylating agents (IIa)-(IIm) as described below.

Reference: [1]Current Patent Assignee: TONGJI UNIVERSITY - CN111961006, 2020, A Location in patent: Paragraph 0028-0033; 0048-0119
[2]Wang, Rong; Cui, Menghan; Yang, Qing; Kuang, Chunxiang [Synthesis, 2021, vol. 53, # 5, p. 978 - 982]
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2006/32453, 2006, A1 Location in patent: Page/Page column 20-21
[4]Uchida; Komatsu; Morita; Kanbe; Yamasaki; Nakagawa [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 4, p. 958 - 961]
[5]Uchida; Komatsu; Morita; Kanbe; Yamasaki; Nakagawa [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 4, p. 958 - 961]
[6]Current Patent Assignee: SYSMEX CORPORATION - EP1506959, 2005, A2 Location in patent: Page 65
[7]Florentino, Lucía; López, Lucía; Barroso, Raquel; Cabal, María-Paz; Valdés, Carlos [Angewandte Chemie - International Edition, 2021, vol. 60, # 3, p. 1273 - 1280][Angew. Chem., 2021, vol. 133, # 3, p. 1293 - 1300,8]
[8]Schliemann; Buege; Reppel [Pharmazie, 1980, vol. 35, # 3, p. 140 - 143]
[9]Matveeva; Kvasha; Kurts [Russian Journal of Organic Chemistry, 1996, vol. 32, # 1, p. 21 - 24]
[10]Lafite, Pierre; Dijols, Sylvie; Buisson, Didier; Macherey, Anne-Christine; Zeldin, Darryl C.; Dansette, Patrick M.; Mansuy, Daniel [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2777 - 2780]
[11]Shen, Yanhong; Sheng, Rong; Zhang, Jing; He, Qiaojun; Yang, Bo; Hu, Yongzhou [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 16, p. 7646 - 7653]
[12]Yu, Feng; Zhou, Ji-Ning; Zhang, Xi-Chang; Sui, Yao-Zong; Wu, Fei-Fei; Xie, Lin-Jie; S. C. Chan, Albert; Wu, Jing [Chemistry - A European Journal, 2011, vol. 17, # 50, p. 14234 - 14240]
[13]Chowdhury, Nilanjana; Dutta, Sansa; Karthick; Anoop, Anakuthil; Dasgupta, Swagata; Pradeep Singh [Journal of Photochemistry and Photobiology B: Biology, 2012, vol. 115, p. 25 - 34]
[14]Komissarov; Valuev-Elliston; Ivanova; Kochetkov; Kritzyn [Russian Journal of Bioorganic Chemistry, 2015, vol. 41, # 1, p. 37 - 45][Bioorg. Khim., 2015, vol. 41, # 1, p. 44 - 53,10]
  • 2
  • [ 100-63-0 ]
  • [ 40877-19-8 ]
  • [ 75343-39-4 ]
YieldReaction ConditionsOperation in experiment
46.4% In ethanol for 3h; Heating;
  • 3
  • [ 13183-79-4 ]
  • [ 40877-19-8 ]
  • [ 80087-39-4 ]
YieldReaction ConditionsOperation in experiment
58% With potassium carbonate In acetone for 3h; Heating;
  • 4
  • [ 42925-01-9 ]
  • [ 40877-19-8 ]
  • [ 130570-14-8 ]
YieldReaction ConditionsOperation in experiment
69% In N,N-dimethyl-formamide for 240h; Ambient temperature;
  • 5
  • [ 42925-01-9 ]
  • [ 40877-19-8 ]
  • [ 130570-19-3 ]
YieldReaction ConditionsOperation in experiment
69% In N,N-dimethyl-formamide for 240h; Ambient temperature;
  • 6
  • [ 130570-22-8 ]
  • [ 40877-19-8 ]
  • [ 130570-09-1 ]
YieldReaction ConditionsOperation in experiment
76% In N,N-dimethyl-formamide for 240h; Ambient temperature;
  • 7
  • [ 82380-53-8 ]
  • [ 40877-19-8 ]
  • [ 130570-20-6 ]
YieldReaction ConditionsOperation in experiment
43% With potassium iodide In N,N-dimethyl-formamide for 240h; Ambient temperature;
  • 8
  • [ 82380-53-8 ]
  • [ 40877-19-8 ]
  • [ 130570-04-6 ]
YieldReaction ConditionsOperation in experiment
69% In N,N-dimethyl-formamide for 240h; Ambient temperature;
  • 9
  • [ 40877-19-8 ]
  • [ 7152-03-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium hydroxide In methanol for 12h; Ambient temperature;
76% With potassium <i>tert</i>-butylate In tetrahydrofuran for 1h; Heating / reflux; 44 Cyclopropyl-(4-methoxyphenyl)-ketone. To a solution of 4-chloro-4'-methoxybutyrophenone (2.13 g, 10 mmol) in dry THF (50 mL) potassium tert-butoxide (1.23 g, 11 mmol) was added and the mixture was refluxed for 1h, then cooled and evporated. The residue was dissolved in EtOAc (100 mL), washed with 5% citric acid (50 mL) and water (50 mL), dried over CaCl2, and evaporated. The residue was purified by column chromatography in toluene to give the desired ketone as a colourless crystalline solid (1.34g, 76%).
54.7% With potassium hydroxide In methanol cooling to 20 deg C;
With potassium hydroxide In ethanol Yield given;

  • 10
  • [ 40877-19-8 ]
  • [ 189079-75-2 ]
YieldReaction ConditionsOperation in experiment
95% With sodium azide In N,N-dimethyl-formamide at 70℃; for 4h; 1.A N-[5-(2-Azido-ethyl)-4-(4-methoxy-phenyl)-thiazol-2-yl]-acetamide ;To a solution of 4-chloro-4'-methoxybutyrophenone (Acros Organics) (22.45 g, 106 mmol) in DMF (300 mL) was added sodium azide (13.7 g, 211 mmol). The solution was heated under N2 (g) at 70° C. for 4 h. The milky reaction mixture was partitioned between ethyl acetate (700 mL) and water (500 mL). The organic layer was washed with another portion of water (500 mL), followed by saturated aqueous sodium bicarbonate (500 mL) and brine (500 mL). The organic layer was dried (sodium sulfate) and concentrated to give an oil (22 g, 95% yield) which solidified slowly upon standing. MS m/e 220; HPLC retention time 3.09 min.
95% With sodium azide In N,N-dimethyl-formamide
95% With sodium azide In DMF (N,N-dimethyl-formamide) at 70℃; for 4h; 1.A 4-Butyl-piperazine-1-sulfonic acid {2-[5-(4-methoxy-phenyl)-2-thiophen-2-yl-1H-imidazol-4-yl]-ethyl}-amide A. 4-Azido-1-(4-methoxy-phenyl)-butan-1-one To a solution of 4-chloro-4'-methoxybutyrophenone (Acros Organics) (22.45 g, 106 mmol) in DMF (300 mL) was added sodium azide (13.7 g, 211 mmol). The solution was heated under N2 (g) at 70° C. for 4 h. The milky reaction mixture was partitioned between ethyl acetate (700 mL) and water (500 mL). The organic layer was washed with another portion of water (500 mL), followed by saturated aqueous sodium bicarbonate (500 mL) and brine (500 mL). The organic layer was dried (sodium sulfate) and concentrated to give an oil (22 g, 95% yield) which solidifed slowly upon standing. MS m/e 220; HPLC retention time 3.09 min.
88% With sodium azide In water; dimethyl sulfoxide for 0.166667h; microwave irradiation;
88% With sodium azide In N,N-dimethyl-formamide at 60℃;
With sodium azide In dimethyl sulfoxide at 55℃; for 12h; Yield given;
With sodium azide In N,N-dimethyl-formamide at 90℃;
With sodium azide In N,N-dimethyl-formamide at 50℃; for 2h; General procedure for the synthesis of γ-azidobutyrophenone (8a-e) General procedure: General procedure for the synthesis of γ-azidobutyrophenone (8a-e) The 4-chlorobutyrophenone 7a (2.5 g, 12.6 mmol) was dissolved in DMF (20 mL) and solid NaN3 (2.1 g, 25.2 mmol) was added and heated up to 50 °C and stirred for 2 h. After completion of the reaction, the reaction mixture was diluted with EtOAc and washed with water. The organic layer was separated and dried with Na2SO4.The solvent was evaporated and purified by column chromatography using pet ether-ethyl acetate (95:5) yielded γ-azidobutyrophenone (8a). The above mentioned procedure was carried out for the synthesis of other γ-azidobutyrophenones (8b-e).

Reference: [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2005/65198, 2005, A1 Location in patent: Page/Page column 12-13
[2]Weinstein, David S.; Liu, Wen; Ngu, Khehyong; Langevine, Charles; Combs, Donald W.; Zhuang, Shaobin; Chen, Cindy; Madsen, Cort S.; Harper, Timothy W.; Robl, Jeffrey A. [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 18, p. 5115 - 5120]
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2005/70588, 2005, A1 Location in patent: Page/Page column 14
[4]Singh, Pradeep N. D.; Muthukrishnan, Sivaramakrishnan; Murthy, Rajesh S.; Klima, Rodney F.; Mandel, Sarah M.; Hawk, Michael; Yarbrough, Nina; Gudmundsdottir, Anna D. [Tetrahedron Letters, 2003, vol. 44, # 51, p. 9169 - 9172]
[5]Florentino, Lucía; López, Lucía; Barroso, Raquel; Cabal, María-Paz; Valdés, Carlos [Angewandte Chemie - International Edition, 2021, vol. 60, # 3, p. 1273 - 1280][Angew. Chem., 2021, vol. 133, # 3, p. 1293 - 1300,8]
[6]De Kimpe, Norbert; Tehrani, Kourosch Abbaspour; Stevens, Christian; De Cooman, Paul [Tetrahedron, 1997, vol. 53, # 10, p. 3693 - 3706]
[7]Location in patent: scheme or table Ngu, Khehyong; Weinstein, David S.; Liu, Wen; Langevine, Charles; Combs, Donald W.; Zhuang, Shaobin; Chen, Xing; Madsen, Cort S.; Harper, Timothy W.; Ahmad, Saleem; Robl, Jeffrey A. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 14, p. 4141 - 4145]
[8]Chowdhury, Nilanjana; Dutta, Sansa; Karthick; Anoop, Anakuthil; Dasgupta, Swagata; Pradeep Singh [Journal of Photochemistry and Photobiology B: Biology, 2012, vol. 115, p. 25 - 34]
  • 11
  • [ 40877-19-8 ]
  • [ 215667-87-1 ]
YieldReaction ConditionsOperation in experiment
79% With sodium iodide In acetone for 16h; Reflux; 57 Preparation of 4-chloro-l -(4-methoxyphenyl)butan-l-one; [0227] Sodium iodide was added to a solution of 4-chloro-l-(4-methoxyphenyl)butan-l-one (1 g, 4.7 mmol, 1 equiv) in acetone, an the reaction mixture was refluxed for 16 h. Upon cooling, the reaction was concentrated in vacuo and the crude mixture was partitioned between dichloromethane and water. The organic layer was dried over MgSO i, filtered and concentrated in vacuo. The residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, R/= 0.7, gradient - 5%>-25%> ethyl acetate in hexanes) to afford the title compound as a brownish green solid (1.13 g, 79%); MS for CUHBCICWZ 214.1 (M+H)+.
75% With sodium iodide In acetone Heating;
With sodium iodide In [(2)H6]acetone for 8h; Reflux;
  • 12
  • [ 40877-19-8 ]
  • [ 22217-80-7 ]
YieldReaction ConditionsOperation in experiment
94% With sodium azide; triethyl phosphite In dimethyl sulfoxide for 0.333333h; microwave irradiation;
Multi-step reaction with 2 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature
  • 14
  • [ 98-03-3 ]
  • [ 40877-19-8 ]
  • (4-methoxy-phenyl)-(2-thiophen-2-yl-tetrahydro-furan-3-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium <i>tert</i>-butylate In ethanol at -18 - 10℃; for 6h;
  • 15
  • [ 100-52-7 ]
  • [ 40877-19-8 ]
  • (4-methoxy-phenyl)-(2-phenyl-tetrahydro-furan-3-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium <i>tert</i>-butylate In ethanol at -18 - 10℃; for 6h;
  • 16
  • [ 75-07-0 ]
  • [ 40877-19-8 ]
  • (4-methoxy-phenyl)-(2-methyl-tetrahydro-furan-3-yl)-methanone [ No CAS ]
  • (4-methoxy-phenyl)-(2-methyl-tetrahydro-furan-3-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In ethanol at -18 - 10℃; for 6h;
  • 17
  • [ 112-31-2 ]
  • [ 40877-19-8 ]
  • (4-methoxy-phenyl)-(2-nonyl-tetrahydro-furan-3-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium <i>tert</i>-butylate In ethanol at -18 - 10℃; for 6h;
  • 18
  • [ 98-86-2 ]
  • [ 4635-59-0 ]
  • C11H12Cl2O [ No CAS ]
  • [ 40877-19-8 ]
YieldReaction ConditionsOperation in experiment
1: 48% 2: 41% at 25℃;
  • 19
  • [ 33397-21-6 ]
  • [ 4635-59-0 ]
  • [ 40877-19-8 ]
YieldReaction ConditionsOperation in experiment
66% With triethylamine In 1,4-dioxane at 80℃; for 3h;
  • 20
  • [ 40877-19-8 ]
  • [ 62170-25-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / NaI / acetone / Heating 2: 72 percent / Ni(acac)2; acetophenone / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 12 h / -35 °C
  • 21
  • [ 40877-19-8 ]
  • [ 4995-12-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: 75 percent / N-bromosuccinimide / CCl4 / 72 h / Ambient temperature 4: NaOMe / methanol / 3 h / Heating
  • 22
  • [ 40877-19-8 ]
  • 3-chloro-2-(4-methoxyphenyl)pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: N-chlorosuccinimide / CCl4 / 1) reflux, 10 min; 2) rt, 14 h 4: NaOMe / methanol / 3 h / Heating
  • 23
  • [ 40877-19-8 ]
  • 3-bromo-2-(4-methoxyphenyl)pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: 22 percent / N-bromosuccinimide / CCl4 / 72 h / Ambient temperature 4: NaOMe / methanol / 3 h / Heating
Multi-step reaction with 4 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: N-bromosuccinimide / CCl4 / 7 h / Heating 4: NaOMe / methanol / 3 h / Heating
  • 24
  • [ 40877-19-8 ]
  • [ 189079-91-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: 75 percent / N-bromosuccinimide / CCl4 / 72 h / Ambient temperature
  • 25
  • [ 40877-19-8 ]
  • [ 189079-85-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: N-chlorosuccinimide / CCl4 / 1) reflux, 10 min; 2) rt, 14 h
  • 26
  • [ 40877-19-8 ]
  • [ 189079-89-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: 22 percent / N-bromosuccinimide / CCl4 / 72 h / Ambient temperature
Multi-step reaction with 3 steps 1: NaN3 / dimethylsulfoxide / 12 h / 55 °C 2: 81 percent / Ph3P / pentane / 14 h / Ambient temperature 3: N-bromosuccinimide / CCl4 / 7 h / Heating
  • 27
  • [ 107-21-1 ]
  • [ 40877-19-8 ]
  • [ 3309-01-1 ]
YieldReaction ConditionsOperation in experiment
41%
With toluene-4-sulfonic acid In benzene for 10h; Reflux; Dean-Stark; Preparation of alkylating agents (IIa)-(IIm) General procedure: A solution of the phenone prepared at the previous step (10 mmol), the corresponding diol (100 mmol),and TSA (0.5 g, 2.6 mmol) were mixed in dry benzene (70 mL). The resulting solution was refluxed for 10 h using a Dean-Stark trap. The reaction mixture was cooled and a solution semisaturated sodium hydrocarbonate (50 mL) was added. The organic layer was separated, and the aqueous phase was extracted with benzene (3 × 30 mL). The united organic extracts were dried with anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by column chromatography (l = 5 cm, d = 5 cm) on silica gel eluting with methylene chloride.
  • 28
  • [ 83072-21-3 ]
  • [ 40877-19-8 ]
  • 4-[4-(4-Chloro-benzyl)-4-hydroxy-piperidin-1-yl]-1-(4-methoxy-phenyl)-butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide In acetonitrile at 100 - 110℃; for 19h; Heating / reflux; 2 Synthesis of 4-[4-(4-Chloro-benzyl)-4-hydroxy-piperidin-1-yl]-1-(4-methoxy-phenyl)-butan-1-one (6) A mixture of 2.11 g of 4-chloro-1-(4-methoxy-phenyl)-butan-1-one (1), 1.60 g of 4-(4-chloro-benzyl)-piperidin-4-ol (5), 1.96 g of K2CO3, and 0.45 g of KI in acetonitrile (50 mL) was stirred and refluxed at 100 to 110°C for 19 hours under nitrogen atmosphere. After the solvent was removed, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and brine and dried over MgSO4. After the solvent was removed, the obtained oily residue was purified by silica gel chromatography (chloroform : methanol = 20/1 to 10/1) and the purified product was recrystallized from AcOEt/Et2O to afford 1.55 g of compound (6). Elemental analysis (%) : C23H28ClNO3· -1/3H2O Calculated : C =67.72, H =7.08, N =3.43, Found : C =67.67, H =6.91, N =3.51,
  • 29
  • [ 192990-05-9 ]
  • [ 40877-19-8 ]
  • 4-[4-Hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-1-(4-methoxy-phenyl)-butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium iodide In acetonitrile at 105 - 110℃; for 9h; Heating / reflux; 1; 3 Synthesis of 4-[4-Hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-1-(4-methoxy-phenyl)-butan-1-one (3) A mixture of 1.62 g of 4-chloro-1-(4-methoxy-phenyl)-butan-1-one (1), 1.20 g of 4-(4-methyl-benzyl)-piperidin-4-ol (2), 1.62 g of K2CO3, and 0.49 g of KI in acetonitrile (30 mL) was stirred and refluxed at 105 to 110°C for 9 hours under nitrogen atmosphere. After the solvent was removed, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and brine and dried over MgSO4. After the solvent was removed, the obtained oily residue was purified by silica gel chromatography (chloroform : methanol = 20/1 to 10/1) and the purified product was recrystallized from AcOEt/Et2O to afford 1.73 g of compound (3). NMR (CDCl3)δ ppm (300 MHz) (Free) 1.45-1.75 (4H, m), 1.936 (2H, quint, J = 7.2Hz), 2.24 - 2.76 (4H, m), 2.324 (3H, s)2.427 (2H, t, J = 6.9Hz), 2.692 (2H, s), 2.935 (2H, t, J = 7.2Hz), 3.865 (3H, s) 6.922 (2H, d, J = 9.0Hz), 7.04 - 7.16 (4H, m), 7.945 (2H,d, J = 9.0Hz)Elemental analysis (%) : C24H31NO · 1/5H2O Calculated value : C = 74.85, H = 8.22, N = 3.64, Experimental value : C = 74.84, H = 8.23, N = 3.85,
  • 30
  • [ 40877-19-8 ]
  • [ 23002-61-1 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran R.3 Production of 1-(4-chlorobutyl)-4-methoxybenzene Reference Example 3 Production of 1-(4-chlorobutyl)-4-methoxybenzene 4-Chloro-1-(4-methoxyphenyl)-1-butanone (5 g, 23.5 mmol) was dissolved in tetrahydrofuran (50 ml). 10% Palladium carbon (water-containing product, 500 mg) was added and the mixture was subjected to catalytic reduction under hydrogen pressure (0.8 MPa, 50° C. for 3 h). The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 1-(4-chlorobutyl)-4-methoxybenzene (4.6 g, yield 99%). 1H-NMR (CDCl3, δ, 300 MHz) 1.69-1.83(4H,m), 2.59(2H,t,J=7.4 Hz), 3.54(2H,t,J=6.2 Hz), 3.79(3H,s), 6.81-6.85(2H,m), 7.08-7.11(2H,m).
  • 31
  • [ 79-19-6 ]
  • [ 40877-19-8 ]
  • 2-[1-(4-methoxy-phenyl)-4-chloro-butylidene]-hydrazinecarbothioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
8.46 g (63%) With hydrogenchloride In methanol; dichloromethane; water 11 2-[1-(4-Methoxy-phenyl)-4-chloro-butylidene]-hydrazinecarbothioamide EXAMPLE 11 2-[1-(4-Methoxy-phenyl)-4-chloro-butylidene]-hydrazinecarbothioamide Thiosemicarbazide (6.4 g, 70 mmol) was added under nitrogen to a solution of 4-chloro-4'-methoxybutyrophenone (10.0 g, 47 mmol) in 150 mL of methanol plus 12.7 mL of 1 N HCl plus 11.8 mL of water and the reaction stirred for approximately three days (over the weekend). The solid formed was collected by filtration and dissolved in methylene chloride. The organic solution was washed multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give a white solid. Recrystallization of the solid from isopropyl alcohol gave 8.46 g (63%) of the title compound as a light yellow solid, mp 137-140° C.
  • 32
  • [ 288-36-8 ]
  • [ 40877-19-8 ]
  • [ 568594-83-2 ]
YieldReaction ConditionsOperation in experiment
53% With potassium iodide at 100℃; for 6h; 10.i i) l-(4-Methoxy-phenyl)-4-[ 1,2,3] triazol-1-yl-butan-l-one. 100 g (0.47 mol) 4-Chloro-l-(4-methoxy-phenyl)-butan-l-one and 1.6 g (9.64 mmol) potassium iodide were mixed with 480 ml (8.4 mol) lH-[l,2,3]Triazole and the mixture was stirred for 6 hours at 100°C. The remaining IH- [1,2,3] Triazole was removed by destination and the residue was dissolved in dichloromethane. The organic layer was washed with 200 ml water, dried over sodium sulfate and evaporated. Recrystallisation (ethyl acetate/n-heptane) gave 85.4 g (53 %) of the title compound as a brown solid. 1H-NMR (400 MHz, [D6]DMSO): δ = 2.14 (quintet, 2H, CH2-CH2-CH2), 2.99 (t, 2H,CO-CH2), 3.84 (s, 3H, 0-CH3), 4.46 (t, 2H, CH2-triazole), 7.03 (d, 2H, Ar), 7.73 (s, IH, triazole), 7.91 (d, 2H, Ar), 8.16 (s, IH, triazole
With sodium hydroxide; potassium iodide In tert-Amyl alcohol at 100℃; for 4h; 1 10.6 g (50 mmol) 4-Chloro-l-(4-methoxy-phenyl)-butan-l-one, 20 ml 2-methyl-2- butanol, 5.2 g (75 mmol) lH-[l,2,3]-triazole, 9.5 g (57 mmol) potassium iodide and 3.0 g (75 mmol) NaOH were stirred at 1000C for 4 h. After removal of solvents in vacuo, the residue was partitioned between toluene and water. Washing of the toluene phase twice with water, drying over sodium sulphate and evaporation gave an oily residue that was dissolved in 80 ml diisopropyl ether/ ethyl acetate (1:2). The solution was kept at 200C during the addition of 2.8 ml methanesulfonic acid and stirred at room temperature for 2h. The formed precipitate was isolated, washed with cold diethyl ether and dried at 400C in vacuo to give l-(4-methoxy- phenyl) -4- [l,2,3]triazol-l-yl-butan-l-one methanesulfonate. Yield: 2.25 g (13%).1H-NMR (400 MHz, Dg-DMSO): δ= 2.16 (quintet, 2H); 2.45 (s, 3H); 3.00 (t, 2H); 3.84 (s, 3H); 4.46 (t, 2H); 7.04 (d, 2H); 7.76 (s, IH); 7.92 (d, 2H); 8.19 (s, IH).
  • 33
  • [ 2759-28-6 ]
  • [ 40877-19-8 ]
  • hydrochloride of 1-(4-methoxyphenyl)-4-[4-phenylmethyl)-1-piperazinyl]-1-butanone [ No CAS ]
  • 1-[1-(4-methoxyphenyl)-4-[4-(phenylmethyl)-1-piperazinyl]-1-butenyl]cyclohexanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In diethyl ether; ethyl acetate; 4-methyl-2-pentanone 10 1-[1-(4-methoxyphenyl)-4-[4-(phenylmethyl)-1-piperazinyl]-1-butenyl]cyclohexanol EXAMPLE 10 1-[1-(4-methoxyphenyl)-4-[4-(phenylmethyl)-1-piperazinyl]-1-butenyl]cyclohexanol A mixture of γ-chloro-p-methoxybutyrophenone (45 g, 210 mole), 1-benzylpiperazine (35 mL, 200 mole) and anhydrous potassium carbonate (250 g) in methylisobutylketone (800 mL) was refluxed under nitrogen for 40 hours. The reaction mixture was cooled, poured into a beaker containing ice, then ethyl acetate was added. The layers were separated. The organic phase was washed with water, brine, dried over K2 CO3 and evaporated to an oil. This residue was dissolved in diethyl ether (200 mL) and treated with excess 4N-isopropanolic HCl. The hydrochloride of 1-(4-methoxyphenyl)-4-[4-phenylmethyl)-1-piperazinyl]-1-butanone was obtained. Wt. 53 g. The product was converted to the free base with NaOH and purified by column chromatography. It was then converted to the dihydrochloride, m.p. 173°-175° C. Elemental Analysis for: C23 H28 N2 O2.2HCl.11/2H2 O Calculated: C, 58.4; H, 6.69; N, 6.19. Found: C, 58.48; H, 7.09; N, 6.05.
  • 34
  • [ 40877-19-8 ]
  • alpha-(4-methoxyphenyl)-beta-(2-chloroethyl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
III EXAMPLE III EXAMPLE III Example I was essentially repeated except that the 6-MT was replaced with 4-methoxyphenyl 3-chloropropyl ketone and the amount of NaCN was reduced to only 1.3 molar proportions. VPC analysis showed a 70% conversion of the ketone to alpha-(4-methoxyphenyl)-beta-(2-chloroethyl)acrylonitrile.
  • 35
  • [ 40877-19-8 ]
  • [ 3309-01-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; toluene-4-sulfonic acid In ethylene glycol; toluene 1.a a) a) Synthesis of 2-(3-chloropropyl)-2-(4-methoxyphenyl)-1,3-dioxolane A solution of 20.0 g (94.0 mmol) of 4-chloro-1-(4-methoxyphenyl)-1-butanone (origin: Acros), 19 ml of ethylene glycol and ca. 1 g of p-toluenesulfonic acid in 120 ml of toluene was heated under reflux with azeotropic removal of water for 16 h. After cooling down to room temperature, ether was added and the organic phase extracted with a saturated solution of NaHCO3 (2*), washed with water (2*), dried (Na2SO4) and concentrated in vacuo to give 24.6 g (99%) of the crude compound, which was used for further functionalization. Column chromatography of 2 g (SiO2, heptane/ether 9:1) afforded 1.15 g of a slightly yellow oil. Analytical data: Rf (heptane/ether 9:1): 0.25 IR (neat): 2956m, 2882m, 2831m, 1610m, 1583m, 1508m, 1463m, 1442m, 1412w, 1372w, 1347w, 1300m, 1239s, 1169s, 1142m, 1108m, 1079w, 1030s, 1009m, 946m, 907m, 855w, 830s, 814m, 800m, 781w, 764w, 746w, 722w. 1H-NMR (360 MHz, CDCl3): 7.39-7.32 (m, 2 H); 6.91-6.83 (m, 2 H); 4.06-3.94 (m, 2 H); 3.84-3.71 (m, 2 H); 3.80 (s, 3 H); 3.52 (t, J=6.7, 2 H); 2.06-1.97 (m, 2 H) 1.91-1.79 (m, 2 H). 13C-NMR (90.6 MHz, CDCl3): 159.34 (s); 134.38 (s); 126.92 (d); 113.49 (d); 109.95 (s); 64.47 (t); 55.25 (q); 45.16 (t); 37.85 (t); 27.16 (t). MS (EI): 256 (M+, 0.4), 180 (18), 179 (100), 149 (4), 136 (7), 135 (68), 121 (3), 107 (6), 92 (7), 77 (8).
  • 36
  • [ 17356-08-0 ]
  • [ 40877-19-8 ]
  • [ 1076160-21-8 ]
YieldReaction ConditionsOperation in experiment
In ethanol for 26h; Heating / reflux; 5.1 [Example 5]; The synthesis of compound 1008; [Show Image] Step 1; The compound (5-1)(3.00 g) was dissolved into ethanol (30 ml), and thiourea (1.13 g) was added, and then the mixture was refluxed for 26 hours, and the solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate/hexane to afford the compound (5-2)(4.03 g). 1H-NMR(DMSO-d6) : 1.95(2H, quint, J=6.8 Hz), 3.13(2H, t, J=6.8 Hz), 3.21(2H, t, J=6.8 Hz), 3.85(3H, s), 7.06(2H, d, J=8.8 Hz), 7.95(2H, d, J=8.8 Hz), 9.18(4H, br).
In ethanol for 26h; Reflux; 5.1 The compound (5-1)(3.00 g) was dissolved into ethanol (30 ml), and thiourea (1.13 g) was added, and then the mixture was refluxed for 26 hours, and the solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate/hexane to afford the compound (5-2)(4.03 g). 1 H-NMR (DMSO-d6) : 1.95(2H, quint, J=6.8 Hz), 3.13(2H, t, J=6.8 Hz), 3.21(2H, t, J=6.8 Hz), 3.85(3H, s), 7.06(2H, d, J=8.8 Hz), 7.95(2H, d, J=8.8 Hz), 9.18(4H, br).
  • 37
  • [ 123-75-1 ]
  • [ 40877-19-8 ]
  • [ 61025-29-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile for 7h; Heating;
  • 38
  • [ 110-89-4 ]
  • [ 40877-19-8 ]
  • [ 61025-28-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile for 7h; Heating;
  • 39
  • [ 624-78-2 ]
  • [ 40877-19-8 ]
  • [ 1009636-11-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile at 100℃; for 5h;
  • 40
  • [ 109-89-7 ]
  • [ 40877-19-8 ]
  • [ 855221-37-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile at 100℃; for 5h;
  • 41
  • [ 40877-19-8 ]
  • [ 343338-28-3 ]
  • [ 1218989-26-4 ]
YieldReaction ConditionsOperation in experiment
85% With titanium (IV) ethoxide In tetrahydrofuran at 65℃; for 48h; Inert atmosphere;
  • 42
  • [ 196929-78-9 ]
  • [ 40877-19-8 ]
  • [ 1227798-52-8 ]
YieldReaction ConditionsOperation in experiment
91% With titanium(IV) tetraethanolate In neat (no solvent) at 72℃; Inert atmosphere;
With titanium(IV) tetraethanolate In tetrahydrofuran Reflux;
  • 43
  • [ 40877-19-8 ]
  • [ 343338-28-3 ]
  • [ 1227798-69-7 ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) tetraethanolate In tetrahydrofuran Reflux;
  • 44
  • [ 40877-19-8 ]
  • [ 1231764-46-7 ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 4-chloro-1-(4-methoxyphenyl)butan-1-one With phosphorus trichloride at 0 - 20℃; Stage #2: With acetic acid at 0 - 20℃; Stage #3: With water at 0 - 90℃;
  • 47
  • [ 40877-19-8 ]
  • [ 849050-98-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: acetic acid; hydrazine / methanol / 70 °C 4: triethylamine / dichloromethane
Multi-step reaction with 5 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C 4: water; triphenylphosphine / tetrahydrofuran / 100 °C 5: triethylamine / dichloromethane
  • 48
  • [ 40877-19-8 ]
  • [ 849051-11-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: acetic acid; hydrazine / methanol / 70 °C 4: triethylamine / dichloromethane
Multi-step reaction with 5 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C 4: water; triphenylphosphine / tetrahydrofuran / 100 °C 5: triethylamine / dichloromethane
  • 49
  • [ 40877-19-8 ]
  • [ 849050-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: acetic acid; hydrazine / methanol / 70 °C 4: triethylamine / dichloromethane
Multi-step reaction with 5 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C 4: water; triphenylphosphine / tetrahydrofuran / 100 °C 5: triethylamine / dichloromethane
  • 50
  • [ 40877-19-8 ]
  • [ 1323995-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C
  • 51
  • [ 40877-19-8 ]
  • [ 1323995-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C
  • 52
  • [ 40877-19-8 ]
  • [ 1323995-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C
  • 53
  • [ 40877-19-8 ]
  • [ 1323995-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C
  • 54
  • [ 40877-19-8 ]
  • [ 1323995-88-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C
  • 55
  • [ 40877-19-8 ]
  • [ 1323995-97-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: acetic acid; hydrazine / methanol / 70 °C
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C 4: water; triphenylphosphine / tetrahydrofuran / 100 °C
  • 56
  • [ 40877-19-8 ]
  • [ 1323995-98-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: acetic acid; hydrazine / methanol / 70 °C
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C 4: water; triphenylphosphine / tetrahydrofuran / 100 °C
  • 57
  • [ 40877-19-8 ]
  • [ 1323995-99-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: acetic acid; hydrazine / methanol / 70 °C
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C 3: hydrazine / methanol / 70 °C 4: water; triphenylphosphine / tetrahydrofuran / 100 °C
  • 58
  • [ 40877-19-8 ]
  • [ 1323996-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C
  • 59
  • [ 40877-19-8 ]
  • [ 1323996-10-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C
  • 60
  • [ 40877-19-8 ]
  • [ 1323996-11-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C
  • 61
  • [ 40877-19-8 ]
  • (-)-4-chloro-1-(4-methoxyphenyl)butan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper diacetate In toluene at -20℃; for 48h; stereoselective reaction;
  • 62
  • [ 40877-19-8 ]
  • [ 1352949-52-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium iodide / acetone / 16 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 68 °C
  • 63
  • [ 40877-19-8 ]
  • 3-((8-(4-(4-methoxyphenyl)-4-oxobutyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium iodide / acetone / 16 h / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 68 °C 3.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C 3.2: pH 5.7
  • 64
  • [ 40877-19-8 ]
  • [ 1207729-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / neat (no solvent) / 72 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-Amino-2-methyl-1-propanol; isopropyl alcohol; potassium <i>tert</i>-butylate / 2 h / 50 °C / Molecular sieve; Inert atmosphere 3: potassium <i>tert</i>-butylate / isopropyl alcohol / 1 h / 50 °C / Inert atmosphere
  • 65
  • [ 40877-19-8 ]
  • C15H24ClNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: titanium(IV) tetraethanolate / neat (no solvent) / 72 °C / Inert atmosphere 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 2-Amino-2-methyl-1-propanol; isopropyl alcohol; potassium <i>tert</i>-butylate / 2 h / 50 °C / Molecular sieve; Inert atmosphere
  • 66
  • [ 40877-19-8 ]
  • [ 1618101-85-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 24 h / -40 - 20 °C 2.1: tert.-butyl lithium / diethyl ether; pentane / 0.17 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere
  • 67
  • [ 40877-19-8 ]
  • [ 1618101-86-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 24 h / -40 - 20 °C 2.1: tert.-butyl lithium / diethyl ether; pentane / 0.17 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere
  • 68
  • [ 40877-19-8 ]
  • [ 1618101-87-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 24 h / -40 - 20 °C 2.1: tert.-butyl lithium / diethyl ether; pentane / 0.17 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere
  • 69
  • [ 100-59-4 ]
  • [ 40877-19-8 ]
  • [ 1618101-91-9 ]
YieldReaction ConditionsOperation in experiment
80% In tetrahydrofuran at -40 - 20℃; for 24h;
  • 70
  • [ 699-19-4 ]
  • [ 40877-19-8 ]
  • [ 21690-63-1 ]
YieldReaction ConditionsOperation in experiment
80% In tetrahydrofuran at -40 - 20℃; for 24h;
  • 71
  • [ 40877-19-8 ]
  • C16H20O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium iodide / [(2)H6]acetone / 8 h / Reflux 2.1: potassium carbonate / acetone / 0.25 h 2.2: Reflux
  • 72
  • [ 40877-19-8 ]
  • methyl 2-diazo-6-(4-methoxyphenyl)-6-oxohexanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium iodide / [(2)H6]acetone / 8 h / Reflux 2.1: potassium carbonate / acetone / 0.25 h 2.2: Reflux 3.1: triethylamine; Methanesulfonyl azide / acetonitrile / 10 h / 0 - 20 °C
  • 73
  • [ 40877-19-8 ]
  • 9-{3-[2-(4-methoxyphenyl)-1,3-dioxolan-2-yl]propyl}adenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / benzene / 10 h / Reflux; Dean-Stark 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 20 h / 80 - 100 °C
  • 74
  • [ 676-58-4 ]
  • [ 40877-19-8 ]
  • [ 1359975-45-3 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: methylmagnesium chloride; 4-chloro-1-(4-methoxyphenyl)butan-1-one In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In tetrahydrofuran; water
  • 75
  • [ 1068-55-9 ]
  • [ 40877-19-8 ]
  • C14H20O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: isopropylmagnesium chloride; 4-chloro-1-(4-methoxyphenyl)butan-1-one In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In tetrahydrofuran; water
  • 76
  • [ 2386-64-3 ]
  • [ 40877-19-8 ]
  • [ 952432-32-5 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: ethylmagnesium chloride; 4-chloro-1-(4-methoxyphenyl)butan-1-one In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In tetrahydrofuran; water
  • 77
  • [ 1888-75-1 ]
  • [ 40877-19-8 ]
  • C14H20O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: isopropyllithium; 4-chloro-1-(4-methoxyphenyl)butan-1-one In diethyl ether; water at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In diethyl ether; water
  • 78
  • [ 811-49-4 ]
  • [ 40877-19-8 ]
  • [ 952432-32-5 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: ethyllithium; 4-chloro-1-(4-methoxyphenyl)butan-1-one In diethyl ether; water at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In diethyl ether; water
  • 79
  • [ 29786-93-4 ]
  • [ 40877-19-8 ]
  • C15H22O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: n-butyllithium; 4-chloro-1-(4-methoxyphenyl)butan-1-one In diethyl ether; water at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In diethyl ether; water
  • 80
  • [ 591-51-5 ]
  • [ 40877-19-8 ]
  • [ 1618101-91-9 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: phenyllithium; 4-chloro-1-(4-methoxyphenyl)butan-1-one In diethyl ether; water at 20℃; for 0.166667h; Stage #2: With sodium hydroxide In diethyl ether; water
Same Skeleton Products
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