Name: 5683-30-7|3-(Trimethylsilyl)propanoic acid|98%
Brand: Ambeed
SKU: A756429
Rating: 90 (28 reviews)

1
[ 4206-67-1 ]
[ 1007476-32-5 ]
[ 5683-30-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	In not given
63%	In not given
	und Spaltung des Reaktionsprodukts mit Alkali;

Reference： [1][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 7, page 23 - 26]
[2]Sommer et al. [Journal of the American Chemical Society, 1949, vol. 71, p. 1509]
[3]Sommer et al. [Journal of the American Chemical Society, 1949, vol. 71, p. 1509]

2
[ 5683-30-7 ]
[ 18187-31-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With thionyl chloride
	With thionyl chloride
	With thionyl chloride In 1,2-dichloro-ethane	8.a a) a) Preparation of 3-trimethylsilylpropanoyl chloride 13.5 g (0.11 mol) of thionyl chloride are added dropwise with stirring to a mixture of 10 9 (0.068 mol) of 3-trimethylsilylpropanoic acid in 30 ml of 1,2-di-chloroethane. The reaction mixture is heated at 40° C. for 2 hours. The excess thionyl chloride is removed by distillation under reduced pressure. The solution obtained is used without further purification for the following step.

90-95	With SOCl₂ In not given
	With oxalyl dichloride at 20℃; for 1.5h;	2 Methoxymethyl(3-trimethylsilyl)propionamide (6) A round-bottomed flask was charged with 3-trimethylsilylpropionic acid (500 mg). Oxalyl chloride (1.45 mL) was added and the reaction mixture was stirred at room temperature for 1.5 hours. The excess of oxalyl chloride was removed under reduced pressure. The acid chloride was used without further purification. Acid chloride and N,O-dimethylhydroxylamine hydrochloride (433 mg) was dissolved in anhydrous methylene chloride. The solution was cooled to 0° C. and pyridine (830 μL) was added. The mixture was stirred at ambient temperature for 2 hours and evaporated in vacuo. The residue was portioned between brine and methylene chloride. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude amide was purified by silica gel column and produced a yield of 612 mg (94%). 1H NMR (300 MHz, CDCl3) δ 3.69 (3H, s), 3.19 (3H, s), 2.42-2.35 (2H, m), 0.86-0.81 (2H, m), 0.024 (9H, s). 13C NMR (75.4 MHz, CDCl3) δ 179.45, 61.40, 26.67, 19.91, 11.39, -1.67.
90-95	With thionyl chloride In not given
	With oxalyl dichloride In tetrahydrofuran at 20℃; for 2h;	A.1 Step 1 To a stirred solution of the 3- (trimethylsilanyl) propionic acid (10 g, 68.5 mmol) in THF (100 ml) was added oxalyl chloride (8.9 ml, 102.7 mmol) and a drop of DMF at room temperature. After stirring for 2 h, the solvent and access of oxalyl chloride was removed under vacuum. The product 3-trimethylsilanylpropionyl chloride was used in the next step without further purification.
90-95	With SOCl₂ In not given

Reference： [1]Nishitani, Kiyoshi; Yamakawa, Koji [Tetrahedron Letters, 1991, vol. 32, # 3, p. 387 - 390]
[2]Sergeeva,Z.I. et al. [Doklady Chemistry, 1960, vol. 134, # 6, p. 1195 - 1197][Doklady Akademii Nauk SSSR, 1960, vol. 134, # 6, p. 1371 - 1373] Sommer; Marans [Journal of the American Chemical Society, 1950, vol. 72, p. 1935,1937,1939]
[3]Current Patent Assignee: L'OREAL SA - US2003/31691, 2003, A1
[4]Sommer, L. H.; Marans, N. S. [Journal of the American Chemical Society, 1950, vol. 72, p. 1935 - 1939] Sommer, L. H.; Rockett, J. [Journal of the American Chemical Society, 1951, vol. 73, p. 5130 - 5134] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 7, page 23 - 26]
[5]Current Patent Assignee: JSR CORPORATION - US8722886, 2014, B1 Location in patent: Page/Page column 14
[6]Current Patent Assignee: DOW INC - US2557802, 1950, A
[7]Current Patent Assignee: QUEST DIAGNOSTICS INC - WO2005/74904, 2005, A2 Location in patent: Page/Page column 52
[8]Current Patent Assignee: DOW INC - US2557802, 1950, A

3
[ 5683-30-7 ]
[ 17865-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; sulfuric acid

Reference： [1]Noll et al. [Journal of the American Chemical Society, 1951, vol. 73, p. 3871]

4
[ 5683-30-7 ]
[ 4608-02-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With H₂SO₄ In sulfuric acid aq. H2SO4;
	With sulfuric acid
	With sulfuric acid In sulfuric acid byproducts: CH4; dropwise addn. of concd. H2SO4 to (CH3)3SiCH2CH2COOH at 10°C; hydrolysis;;

	With H₂SO₄ In sulfuric acid byproducts: CH4; aq. H2SO4; dropwise addn. of concd. H2SO4 to (CH3)3SiCH2CH2COOH at 10°C; hydrolysis;;
	With sulfuric acid

Reference： [1]Sommer et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 2932] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 93, page 253 - 257]
[2]Sommer et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 2932]
[3]Sommer et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 3765]
[4]Sommer, L. H.; Marans, N. S.; Goldberg, G. M.; Rockett, J.; Pioch, R. P. [Journal of the American Chemical Society, 1951, vol. 73, p. 882 - 882] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 7, page 23 - 26]
[5]Current Patent Assignee: DOW INC - US2589446, 1949, A

5
[ 17728-88-0 ]
[ 5683-30-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide In ethanol

Reference： [1]Nishitani, Kiyoshi; Yamakawa, Koji [Tetrahedron Letters, 1991, vol. 32, # 3, p. 387 - 390]
[2]Sommer; Marans [Journal of the American Chemical Society, 1950, vol. 72, p. 1935,1937,1939]

6
[ 18151-32-1 ]
[ 5683-30-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide; dihydrogen peroxide In water Heating;

Reference： [1]Fleming, Ian; Goldhill, Jon [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1493 - 1498]
[2]Nozakura; Konotsune [Bulletin of the Chemical Society of Japan, 1956, vol. 29, p. 326,330] Petrow et al. [Doklady Akademii Nauk SSSR, 1955, vol. 100, p. 711,713][Chem.Abstr., 1955, p. 1574]

7
[ 5683-31-8 ]
[ 58207-98-0 ]
[ 5683-30-7 ]
[ 88946-47-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 3351 - 3362
[2]Journal of the Chemical Society. Perkin transactions I,1992,p. 3351 - 3362

8
[ 5683-31-8 ]
[ 5683-30-7 ]
[ 88946-47-8 ]

Reference： [1]Chemische Berichte,1988,vol. 121,p. 1151 - 1158

9
[ 5683-30-7 ]
[ 124-68-5 ]
[ 122069-94-7 ]

Yield	Reaction Conditions	Operation in experiment
60.4%	Heating;

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

10
[ 201230-82-2 ]
[ 754-05-2 ]
[ 5683-30-7 ]

Yield	Reaction Conditions	Operation in experiment
95 % Chromat.	With water In tetrahydrofuran at 90℃; for 16h; other temperatures, other solvents, other Pd(II)-catalysts, other vinylsilanes; β-regioselectivity/regiospecifity of hydrocarboxylation;
95 % Chromat.	With water In tetrahydrofuran at 90℃; for 16h;

Reference： [1]Takeuchi, Ryo; Ishii, Naomi; Sugiura, Masaharu; Sato, Nobuhiro [Journal of Organic Chemistry, 1992, vol. 57, # 15, p. 4189 - 4194]
[2]Takeuchi, Ryo; Ishii, Naomi; Sugiura, Masaharu; Sato, Nobuhiro [Journal of Organic Chemistry, 1992, vol. 57, # 15, p. 4189 - 4194]

11
[ 201230-82-2 ]
[ 754-05-2 ]
[ 5683-30-7 ]
[ 57025-63-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 46 % Chromat. 2: 1 % Chromat.	With water In tetrahydrofuran at 120℃; for 16h;

Reference： [1]Takeuchi, Ryo; Ishii, Naomi; Sugiura, Masaharu; Sato, Nobuhiro [Journal of Organic Chemistry, 1992, vol. 57, # 15, p. 4189 - 4194]

12
[ 5683-30-7 ]
[ 100-51-6 ]
[ 83182-24-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 4 A molecular sieve; toluene-4-sulfonic acid In toluene for 6h; Heating;

Reference： [1]Fleming, Ian; Goldhill, Jon; Perry, David A. [Journal of the Chemical Society. Perkin transactions I, 1982, # 7, p. 1563 - 1570]

13
[ 151-50-8 ]
[ 83578-66-9 ]
[ 5683-30-7 ]
[ 147226-62-8 ]
2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-4-trimethylsilanyl-but-3-enenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 9% 2: 62% 3: 4%	With tetrabutylphosphine bromide; water In dichloromethane at 20℃; for 12h;

Reference： [1]Takeda, Kei; Ohnishi, Yuji [Tetrahedron Letters, 2000, vol. 41, # 21, p. 4169 - 4172]

14
[ 5272-36-6 ]
[ 5683-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / CrO₃ / acetone; aq. H₂SO₄ / 14 h / Ambient temperature 2: H₂, quinoline / Lindlar-cat. / hexane / Ambient temperature

Reference： [1]Hermeling, Dieter; Schaefer, Hans J. [Chemische Berichte, 1988, vol. 121, p. 1151 - 1158]

15
[ 5683-30-7 ]
[ 18387-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) LiH / 1) Et₂O, -78 deg C, 4 h then RT, overnight, 2) Et₂O, -78 deg C, 4 h 2: 83.8 percent / LiAlH₄ / diethyl ether / 0 - 20 °C / var. reag.: (R)-Alpine-hydride

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. [Journal of the American Chemical Society, 1987, vol. 109, # 3, p. 804 - 809]

16
[ 5683-30-7 ]
[ 106359-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) LiH / 1) Et₂O, -78 deg C, 4 h then RT, overnight, 2) Et₂O, -78 deg C, 4 h 2: LiAlD₄ / diethyl ether / 0 - 20 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. [Journal of the American Chemical Society, 1987, vol. 109, # 3, p. 804 - 809]

17
[ 5683-30-7 ]
[ 106359-09-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) LiH / 1) Et₂O, -78 deg C, 4 h then RT, overnight, 2) Et₂O, -78 deg C, 4 h 2: 51.6 percent / D₂O, Na₂CO₃ / Heating 3: LiAlH₄ / diethyl ether / 0 - 20 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. [Journal of the American Chemical Society, 1987, vol. 109, # 3, p. 804 - 809]

18
[ 5683-30-7 ]
[ 106359-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) LiH / 1) Et₂O, -78 deg C, 4 h then RT, overnight, 2) Et₂O, -78 deg C, 4 h 2: 51.6 percent / D₂O, Na₂CO₃ / Heating

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. [Journal of the American Chemical Society, 1987, vol. 109, # 3, p. 804 - 809]

19
[ 5683-30-7 ]
[ 106359-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) LiH / 1) Et₂O, -78 deg C, 4 h then RT, overnight, 2) Et₂O, -78 deg C, 4 h 2: 83.8 percent / LiAlH₄ / diethyl ether / 0 - 20 °C / var. reag.: (R)-Alpine-hydride 3: 30 percent / pyridine / 24 h / -10 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. [Journal of the American Chemical Society, 1987, vol. 109, # 3, p. 804 - 809]

20
[ 5683-30-7 ]
[ 106359-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) LiH / 1) Et₂O, -78 deg C, 4 h then RT, overnight, 2) Et₂O, -78 deg C, 4 h 2: LiAlD₄ / diethyl ether / 0 - 20 °C 3: 30 percent / pyridine / 24 h / -10 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. [Journal of the American Chemical Society, 1987, vol. 109, # 3, p. 804 - 809]

21
[ 5683-30-7 ]
[ 106359-14-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1) LiH / 1) Et₂O, -78 deg C, 4 h then RT, overnight, 2) Et₂O, -78 deg C, 4 h 2: 51.6 percent / D₂O, Na₂CO₃ / Heating 3: LiAlH₄ / diethyl ether / 0 - 20 °C 4: 30 percent / pyridine / 24 h / -10 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. [Journal of the American Chemical Society, 1987, vol. 109, # 3, p. 804 - 809]

22
[ 1066-54-2 ]
[ 5683-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) methylmagnesium bromide / 1.) THF, Et₂O, rt, 2h 2.) a) -23 deg C, 30 min b) rt, 2 h 2: H₂, quinoline / Pd (10percent on BaSO₄) / methanol / 7 h / Ambient temperature

Reference： [1]Fleming, Ian; Gil, Salvador; Sarkar, Achintya K.; Schmidlin, Tibur [Journal of the Chemical Society. Perkin transactions I, 1992, # 24, p. 3351 - 3362]

23
[ 5683-30-7 ]
[ 18388-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

24
[ 5683-30-7 ]
[ 1035817-15-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 83.1 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

25
[ 5683-30-7 ]
1,1,1,3-Tetradeuterio-3,5,5-trimethyl-5-sila-2-hexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 30 percent / D₂O, PCl₅ / 528 h / Ambient temperature 5: 74 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

26
[ 5683-30-7 ]
[ 122092-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 30 percent / D₂O, PCl₅ / 528 h / Ambient temperature

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

27
[ 5683-30-7 ]
1,1,1,3-Tetradeuterio-3,5,5-trimethyl-5-sila-2-hexyl p-bromobenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 30 percent / D₂O, PCl₅ / 528 h / Ambient temperature 5: 74 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C 6: 61 percent / pyridine / 1.) 0 deg C, 30 min, 2.) -10 deg C, 3 d

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

28
[ 5683-30-7 ]
2-Deuterio-3,5,5-trimethyl-5-sila-2-hexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

29
[ 5683-30-7 ]
threo-2-Deuterio-3,5,5-trimethyl-5-sila-2-hexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C 5: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature 6: 95 percent / LiOH / methanol / 3 h

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

30
[ 5683-30-7 ]
erythro-2-Deuterio-3,5,5-trimethyl-5-sila-2-hexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C 5: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature 6: 91 percent / LiOH / methanol / 3 h

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

31
[ 5683-30-7 ]
threo-3,5,5-Trimethyl-5-sila-2-hexyl brosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 83.1 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C 5: pyridine / 1.) 0 deg C, 30 min, 2.) -10 deg C, 3 d

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

32
[ 5683-30-7 ]
erythro-3,5,5-Trimethyl-5-sila-2-hexyl brosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 83.1 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C 5: pyridine / 1.) 0 deg C, 30 min, 2.) -10 deg C, 3 d

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

33
[ 5683-30-7 ]
threo-2-Deuterio-3,5,5-trimethyl-5-sila-2-hexyl-p-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C 5: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

34
[ 5683-30-7 ]
erythro-2-Deuterio-3,5,5-trimethyl-5-sila-2-hexyl-p-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C 5: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

35
[ 5683-30-7 ]
threo-2-Deuterio-3,5,5-trimethyl-5-sila-2-hexyl p-bromobenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C 5: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature 6: 95 percent / LiOH / methanol / 3 h 7: pyridine / 1.) 0 deg C, 30 min, 2.) -10 deg C, 3 d
	Multi-step reaction with 5 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C 5: 53 percent / pyridine / 1.) 0 deg C, 30 min, 2.) -10 deg C, 3 d

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]
[2]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

36
[ 5683-30-7 ]
erythro-2-Deuterio-3,5,5-trimethyl-5-sila-2-hexyl p-bromobenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 60.4 percent / Heating 2: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) -78 deg C, 5 h 4: 70.9 percent / LiAlD₄ / diethyl ether / 2 h / 0 °C 5: Et₃N, (dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature 6: 91 percent / LiOH / methanol / 3 h 7: pyridine / 1.) 0 deg C, 30 min, 2.) -10 deg C, 3 d

Reference： [1]Shiner, V. J.; Ensinger, Mark W.; Huffman, John C. [Journal of the American Chemical Society, 1989, vol. 111, # 18, p. 7199 - 7205]

37
[ 5683-30-7 ]
[ 111-27-3 ]
C₁₂H₂₆O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane at 70℃; for 24h; Heating / reflux;	1 Example 1 Novozyme 435 (N435), Candida cylindricia (CCL), and porcine pancreatic (PPL) lipase were used to catalyze the esterification of trimethylsilylpropionic acid with hexanol as shown in the following diagram: O N435 HOC6H3 (CH3) 6 H13 (CH-1-oc H + Ho hexane 70C 24 hours The reactions were conducted with constant stirring (i. e. magnetic stir bar) in a two-neck round-bottom flask attached to a Dean-Stark trap and a water-cooled condenser in a heated oil bath. The reactions were performed in refluxing hexane (i. e. [70C] pot, [90C] bath temperature). The organic reactant was added to the organosilicon-solvent solution at [70C.] After homogenization, the dried enzyme was added to the reaction mixture and the reactions were conducted for 24 hours. The reactions were formulated with [ORGANOSILICON] : organic and solvent : monomer mole ratios equal to 1: 1 and 10: 1, respectively. The enzyme: monomer weight ratio was 1: 10. The lipases formed heterogeneous suspensions in the stirred organic mixtures. In the presence of the Dean-Stark trap, the formation of a hexane-water azeotrope further promoted the esterification reactions. After the reaction, chloroform (-10 mL) was added to the mixture to remove the contents from the flask and filter out the enzyme. Subsequently, the filtrate was evaporated on a rotary evaporator and dried in a vacuum oven overnight at [~45C] in order to isolate the product. The reactions were characterized [BY 1H] and 13C nuclear magnetic resonance spectroscopy (NMR), gas chromatography-mass spectrometry (GC-MS), gas chromatography-flame ionization detection (GC- [FID),] and electrospray mass spectrometry (ESI MS). Fig. [1] illustrates the [13C] NMR of the esterification. Fig. 2 illustrates the GC-MS of the esterification. Based on the analyses, lipase was observed to catalyze the esterification reaction. Comparatively, N435 was determined to be more active than CCL or PPL. The materials were observed to contain a mixture of products and reactants.
	In hexane at 70℃; for 24h; Heating / reflux;	1 Example 1 Novozyme 435 (N435), Candida cylindricia (CCL), and porcine pancreatic (PPL) lipase were used to catalyze the esterification of trimethylsilylpropionic acid with hexanol as shown in the following diagram: O N435 HOC6H3 (CH3) 6 H13 (CH-1-oc H + Ho hexane 70°C 24 hours The reactions were conducted with constant stirring (i. e. magnetic stir bar) in a two-neck round-bottom flask attached to a Dean-Stark trap and a water-cooled condenser in a heated oil bath. The reactions were performed in refluxing hexane (i. e. [70°C] pot, [90°C] bath temperature). The organic reactant was added to the organosilicon-solvent solution at [70°C.] After homogenization, the dried enzyme was added to the reaction mixture and the reactions were conducted for 24 hours. The reactions were formulated with [ORGANOSILICON] : organic and solvent : monomer mole ratios equal to 1: 1 and 10: 1, respectively. The enzyme: monomer weight ratio was 1: 10. The lipases formed heterogeneous suspensions in the stirred organic mixtures. In the presence of the Dean-Stark trap, the formation of a hexane-water azeotrope further promoted the esterification reactions. After the reaction, chloroform (-10 mL) was added to the mixture to remove the contents from the flask and filter out the enzyme. Subsequently, the filtrate was evaporated on a rotary evaporator and dried in a vacuum oven overnight at [~45°C] in order to isolate the product. The reactions were characterized [BY 1H] and 13C nuclear magnetic resonance spectroscopy (NMR), gas chromatography-mass spectrometry (GC-MS), gas chromatography-flame ionization detection (GC- [FID),] and electrospray mass spectrometry (ESI MS). Fig. [1] illustrates the [13C] NMR of the esterification. Fig. 2 illustrates the GC-MS of the esterification. Based on the analyses, lipase was observed to catalyze the esterification reaction. Comparatively, N435 was determined to be more active than CCL or PPL. The materials were observed to contain a mixture of products and reactants.
	In hexane at 70℃; for 24h; Heating / reflux;	1 Example 1 Novozyme 435 (N435), Candida cylindricia (CCL), and porcine pancreatic (PPL) lipase were used to catalyze the esterification of trimethylsilylpropionic acid with hexanol as shown in the following diagram: O N435 HOC6H3 (CH3) 6 H13 (CH-1-oc H + Ho hexane 70°C 24 hours The reactions were conducted with constant stirring (i. e. magnetic stir bar) in a two-neck round-bottom flask attached to a Dean-Stark trap and a water-cooled condenser in a heated oil bath. The reactions were performed in refluxing hexane (i. e. [70°C] pot, [90°C] bath temperature). The organic reactant was added to the organosilicon-solvent solution at [70°C.] After homogenization, the dried enzyme was added to the reaction mixture and the reactions were conducted for 24 hours. The reactions were formulated with [ORGANOSILICON] : organic and solvent : monomer mole ratios equal to 1: 1 and 10: 1, respectively. The enzyme: monomer weight ratio was 1: 10. The lipases formed heterogeneous suspensions in the stirred organic mixtures. In the presence of the Dean-Stark trap, the formation of a hexane-water azeotrope further promoted the esterification reactions. After the reaction, chloroform (-10 mL) was added to the mixture to remove the contents from the flask and filter out the enzyme. Subsequently, the filtrate was evaporated on a rotary evaporator and dried in a vacuum oven overnight at [~45°C] in order to isolate the product. The reactions were characterized [BY 1H] and 13C nuclear magnetic resonance spectroscopy (NMR), gas chromatography-mass spectrometry (GC-MS), gas chromatography-flame ionization detection (GC- [FID),] and electrospray mass spectrometry (ESI MS). Fig. [1] illustrates the [13C] NMR of the esterification. Fig. 2 illustrates the GC-MS of the esterification. Based on the analyses, lipase was observed to catalyze the esterification reaction. Comparatively, N435 was determined to be more active than CCL or PPL. The materials were observed to contain a mixture of products and reactants.

Reference： [1]Current Patent Assignee: DOW INC; NEW YORK UNIVERSITY - WO2004/16625, 2004, A2 Location in patent: Page 20-21
[2]Current Patent Assignee: DOW INC; NEW YORK UNIVERSITY - WO2004/16625, 2004, A2 Location in patent: Page 20-21
[3]Current Patent Assignee: DOW INC; NEW YORK UNIVERSITY - WO2004/16625, 2004, A2 Location in patent: Page 20-21

38
[ 111-26-2 ]
[ 5683-30-7 ]
C₁₂H₂₇NOSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	In hexane at 70℃; for 144h; Heating / reflux;	9 Example 9 Subtilisin (i. e. , a protease) was used to catalyze the formation of an amide bond between trimethylsilylpropionic acid and hexyl amine as shown in the following diagram: dz0 subtdisin ; I (CH3) 3Si OH + HaN--C (CH3) 3Si hexane 70°C 6 days The reaction was conducted using hexane as a solvent. The reaction was conducted with constant stirring (i. e. magnetic stir bar) in a two-neck round-bottom flask attached to a Dean-Stark trap and a water-cooled condenser in a heated oil bath. The hexane reaction was formulated with [ORGANOSILICON] : organic and solvent : monomer mole ratios equal to 1: 1 and 10: 1, respectively. The enzyme: monomer weight ratio was 1: 10. The protease formed a heterogeneous suspension in the stirred organic mixture. The hexyl amine was added to the trimethylsilylpropionic acid at [70°C.] After homogenization, dried subtilisin was added to the reaction mixture and heated for 12 hours. The refluxing reaction in hexane was conducted at [70°C] for 6 days. The completion of the reaction was monitored [BY'H] NMR or thin layer chromatography (TLC). After the reaction, chloroform was added to the mixture to remove the contents from the flask and filter out the enzyme. Subsequently, the filtrate was evaporated on a rotary evaporator and dried in a vacuum oven overnight [AT ~45°C] in order to isolate the product. The reaction was characterized by [13C] NMR. Based on the spectral results, subtilisin was observed to catalyze the formation of an amide bond. The yield was estimated to be approximately 20%.

Reference： [1]Current Patent Assignee: DOW INC; NEW YORK UNIVERSITY - WO2004/16625, 2004, A2 Location in patent: Page 28-29

39
[ 79-37-8 ]
[ 5683-30-7 ]
[ 18187-31-0 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; N,N-dimethyl-formamide	1.B Step B Step B Synthesis of 4,4-dimethyl-4-silapentanoic acid chloride In a flask were place 13.4 g (0.0918 mole) of 4,4-dimethyl-4-silapentanoic acid, 100 mL of diethyl ether, and two drops of N,N-dimethylformamide. To this solution, which was cooled in an ice/water bath, was added 13.98 g (0.110 mole) of oxalyl chloride in diethyl ether in a dropwise manner. Upon completion of addition, the temperature was allowed to rise to ambient conditions, and the mixture was stirred for approximately 16 hours. At the conclusion of this period the solvent was evaporated from the reaction mixture under reduced pressure, leaving 10.42 g of 4,4-dimethyl-4-silapentanoic acid chloride as a residue. The NMR spectrum was consistent with the proposed structure.

Reference： [1]Current Patent Assignee: FMC CORP - US5502054, 1996, A

40
4-(2,4-dichlorophenyl)-1-butanol [ No CAS ]
[ 5683-30-7 ]
[ 66648-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In water; acetone	4.C Step C Step C Synthesis of 4-(2,4-dichlorophenyl)butanoic acid By the method of Example 1, Step A, 3.63 g (0.0363 mole) of chromium trioxide, 5 mL of water, 5.6 g (0.056 mole) of 18M sulfuric acid, 10.4 mL of water, and 11.4 g (0.052 mole) of 4-(2,4-dichlorophenyl)-1-butanol in 332 mL of acetone are reacted, yielding 4-(2,4-dichlorophenyl)butanoic acid.

Reference： [1]Current Patent Assignee: FMC CORP - US5502054, 1996, A

41
[ 996-82-7 ]
[ 2344-80-1 ]
[ 5683-30-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	In not given refluxing of (CH3)3SiCH2Cl and NaCH(COOC2H5)2; hydrolysis with 50% KOH; treatment with concd. HCl;;
65%	In not given refluxing of (CH3)3SiCH2Cl and NaCH(COOC2H5)2; hydrolysis with 50% KOH; treatment with concd. HCl;;
65%	In not given refluxing of (CH3)3SiCH2Cl and NaCH(COOC2H5)2; hydrolysis with 50% KOH; treatment with concd. HCl;;

Reference： [1]Current Patent Assignee: DOW INC - US2557802, 1950, A [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 7, page 23 - 26]
[2]Sommer et al. [Journal of the American Chemical Society, 1949, vol. 71, p. 1509]
[3]Current Patent Assignee: DOW INC - US2557802, 1950, A

42
[ 5683-30-7 ]
[ 619-45-4 ]
[ 1112416-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	1.G Methyl 4-[3-trimethylsilyl)propanoyl]amino}benzoate. To a solution of 3-(trimethylsilyl)propanoic acid (0.500 g, 3.42 mmol) in DCM (10 mL) was added EDC (1.97 g, 10.26 mmol), HOBt (1.57 g, 10.26mmol) and methyl 4-aminobenzoate (1.55g, 10.26 mmol). The reaction was allowed to stir at room temperature for 18 h, diluted with DCM, washed with sat'd NaHCO3, dried (MgSO4), filtered and concentrated in vacuo. The filtrate was purified by MPLC (0-100% DCM/EtOAc) to give the desired product. 1H NMR (d6-DMSO, 600 MHz) δ 10.17 (s, IH), 7.87 (dd, J = 7.2, 1.8 Hz, 2H), 7.70 (dd, J = 6.6, 1.8 Hz, 2H), 7.60 (dd, J = 6.6, 1.8 Hz, 3H), 6.53 (dd, J = 6.6, 1.8 Hz, 3H), 5.94 (br s, 3H), 3.79 (s, 3H), 2.30 (m, 2H), 0.79 (m, 2H), 0.054 (s, 9H). MS: cal'd 280 (MH+), exp 280 (MH+).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/20589, 2009, A1 Location in patent: Page/Page column 70

43
[ 5683-30-7 ]
C₂₉H₃₀N₄O₃S [ No CAS ]
[ 1112416-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 12h;	1.H λf-[2-Amino-5-(2-thienyl)phenyl]-4-({(pyridin-3-ylmethyl)[3-(trimethylsilyl)propanoyl]amino} methyl)benzamide. A mixture of 1,1-dimethylethyl [2-([4-(bromomethyl)phenyl]carbonyl}amino)-4- (2-thienyl)phenyl]carbamate (220 mg, 0.451 mmol) and 3-aminomethylpyridine (100 mg, 0.925 mmol) in 2 mL of DMF was stirred overnight, diluted with EtOAc and washed with 2N NaOH, water, dried (Na2SO4), and finally concentrated. The amine was then dissolved in 2 mL of DMF and treated with TMSCH2CH2CO2H (100 mg, 0.684 mmol), HOBt (150 mg, 0.980 mmol) and EDC (200 mg, 1.04 mmol). The mixture was stirred for 12 hours, diluted with EtOAc and washed with sat'd NaHCO3, dried (Na2SO4), concentrated. Chromatography on SiO2 (0-100% EtOAc/DCM) gave the intermediate Boc- protected anilide which was finally treated with 1 :1 TFA/DCM and stirred for 1 hour. The reaction mixture was diluted with DCM and washed with sat'd NaHCO3, dried (Na2SO4), and concentrated giving the title compound. 1H NMR (d6-DMSO, 600 MHz) δ 9.73 and 9.69 (2s, 1 H), 8.45 (m, 2 H), 7.96 (m, 2 H), 7.65 and 7.60 (2d, J = 7.9 Hz, 1 H), 7.45 (s, 1 H), 7.27-7.40 (m, 5 H), 7.22 (d, J = 3.5 Hz, 1 H), 7.03 (dd, J = 4.9, 3.5 Hz, 1 H), 6.79 (d, J= 8.2 Hz, 1 H), 5.22 (br, 2 H), 4.61 (m, 4 H), 2.34 (m, 2 H), 0.72 (m, 2 H), -0.09 (s, 9 H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/20589, 2009, A1 Location in patent: Page/Page column 71-72

44
[ 5683-30-7 ]
[ 18151-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ / not given 2: NH₃ / not given 3: P₂O₅ / neat (no solvent)
	Multi-step reaction with 3 steps 1: SOCl₂ / not given 2: NH₃ / not given 3: P₂O₅ / neat (no solvent)
	Multi-step reaction with 3 steps 1: thionyl chloride / not given 2: ammonia / not given 3: phosphorus pentoxide / neat (no solvent)

Reference： [1]Sommer, L. H.; Rockett, J. [Journal of the American Chemical Society, 1951, vol. 73, p. 5130 - 5134]
[2]Current Patent Assignee: DOW INC - US2557802, 1950, A [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 7, page 23 - 26]
[3]Current Patent Assignee: DOW INC - US2557802, 1950, A

45
[ 5683-30-7 ]
[ 18091-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / not given 2: NH₃ / not given
	Multi-step reaction with 2 steps 1: SOCl₂ / not given 2: NH₃ / not given
	Multi-step reaction with 2 steps 1: thionyl chloride / not given 2: ammonia / not given

Reference： [1]Current Patent Assignee: DOW INC - US2557802, 1950, A [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 7, page 23 - 26]
[2]Sommer, L. H.; Marans, N. S. [Journal of the American Chemical Society, 1950, vol. 72, p. 1935 - 1939] Sommer, L. H.; Rockett, J. [Journal of the American Chemical Society, 1951, vol. 73, p. 5130 - 5134]
[3]Current Patent Assignee: DOW INC - US2557802, 1950, A

46
[ 5683-30-7 ]
[ 13506-99-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / not given 2: not given
	Multi-step reaction with 2 steps 1: SOCl₂ / not given 2: not given

Reference： [1][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 7, page 23 - 26]
[2]Sommer, L. H.; Marans, N. S. [Journal of the American Chemical Society, 1950, vol. 72, p. 1935 - 1939]

47
[ 5683-30-7 ]
(S)-3-((3,5-dimethoxyphenyl)ethynyl)-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
(S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-yn-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.7 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide	5 Synthesis of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-yn-1-one (compound of Example 5) The crude product (16 mg) of (S)-3-((3,5-dimethoxyphenyl)ethynyl)-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine obtained in Example 2 as an intermediate, 3-(trimethylsilyl)propionic acid (10 mg), HATU (28 mg) were dissolved in DMF (0.5 ml). DIPEA (31 μl) was added thereto, followed by stirring overnight. Ethyl acetate and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture to separate the organic layer. After drying the organic layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol) to obtain the title compound as a white solid (0.7 mg)
0.7 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide	5 Synthesis of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-yn-1-one (compound of Example 5) The crude product (16 mg) of (S)-3-((3,5-dimethoxyphenyl)ethynyl)-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine obtained in Example 2 as an intermediate, 3-(trimethylsilyl)propionic acid (10 mg), HATU (28 mg) were dissolved in DMF (0.5 ml). DIPEA (31 μl) was added thereto, followed by stirring overnight. Ethyl acetate and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture to separate the organic layer. After drying the organic layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol) to obtain the title compound as a white solid (0.7 mg). Table 2 shows the physical properties thereof.
0.7 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide	5 Synthesis of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-yn-1-one The crude product (16 mg) of (S)-3-((3,5-dimethoxyphenyl)ethynyl)-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine obtained in Example 2 as an intermediate, 3-(trimethylsilyl)propionic acid (10 mg), HATU (28 mg) were dissolved in DMF (0.5 ml). DIPEA (31 μl) was added thereto, followed by stirring overnight. Ethyl acetate and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture to separate the organic layer. After drying the organic layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol) to obtain the title compound as a white solid (0.7 mg). Table 2 shows the physical properties thereof

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP2657233, 2013, A1 Location in patent: Paragraph 0201
[2]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - US2016/136168, 2016, A1 Location in patent: Paragraph 0292
[3]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - US2016/193210, 2016, A1 Location in patent: Paragraph 0294

48
[ 5683-30-7 ]
(5-morpholino-4-ylpyrimidin-2-yl)hydrazine [ No CAS ]
trimethylsilyl-N'-(5-morpholin-4-ylpyrimidin-2-yl)propynehydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.98 g	Stage #1: 3-trimethylsilylpropionic acid With 4-methyl-morpholine; isopropyl chloroformate In ethyl acetate at 20℃; for 3h; Stage #2: (5-morpholino-4-ylpyrimidin-2-yl)hydrazine In tetrahydrofuran at 20℃; for 0.5h;	3.6 Step Six: trimethylsilyl-N'-(5-morpholin-4-ylpyrimidin-2-yl)propynehydrazide 3-methyl-silicon propiolate (1.49g, 14.478mmol) and 4-methylmorpholine (0.97mL, 8.86mmol) was dissolved in anhydrous ethyl acetate (30mL), to which was added isopropyl chloroformate (2M solution, 4.43mL, 8.86mmo 1), stirred at room temperature after 3h, the organic phase is washed with water and saturated sodium chloride solution, saturated sodium bicarbonate solution, the organic phase was evaporated to dryness, and the residue was dissolved in dry tetrahydrofuran (20 mL) , thereto was slowly added (5-morpholin-2-yl) hydrazine (1.57g, 8.06mmol), stirred at room temperature 0.5h, after the end of the reaction by TLC, water was added thereto, and extracted with methylene chloride, dried over anhydrous sulfate The organic phase was dried over sodium, filtered and the solvent was evaporated to dryness, purified by silica gel column chromatography to give (trimethylsilyl) - propionic acid N '- (5- morpholin-4-yl morphine - pyrimidin-2-yl) - hydrazide (yellow solid , 1.98g)

Reference： [1]Current Patent Assignee: SHANGHAI PHARMACEUTICALS HOLDING COMPANY LIMITED - CN103420977, 2016, B Location in patent: Paragraph 0211-0212; 0223-0224

49
[ 5683-30-7 ]
5-cyclopropyl-pyridin-2-ylhydrazine [ No CAS ]
(trimethylsilyl)-N'-(5-cyclopropylpyridin-2-yl)prop-2-ynehydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.11 g	Stage #1: 3-trimethylsilylpropionic acid With 4-methyl-morpholine; isopropyl chloroformate In ethyl acetate for 3h; Cooling with ice; Stage #2: 5-cyclopropyl-pyridin-2-ylhydrazine In tetrahydrofuran at 20℃; for 0.5h;	4.3 The third step: (trimethylsilyl)-N'-(5-cyclopropylpyridin-2-yl)prop-2-ynehydrazide trimethylsilylpropionic acid (0.41 g, 2.86 mmol), 4- methylmorpholine (0.29 mL, 2.6 mmol) wasdissolved in ethyl acetate (10 mL), to which was added isopropyl chloroformate( 2M, 1.3 mL, 2.6 mmol), stirred at room temperature after 3h, the reactionsolution was washed with water, washed with saturated NaHC0 3 solutionand saturated NaCl solution, the organic phase was evaporated to dryness, andthe residue was dissolved in THF (lO mL), to which was added slowly ( 5-cyclopropyl-2-yl) hydrazine (0.35 g, 2.34 mmol), stirred at room temperature0.5h, after the end of the reaction by TLC, water was added thereto, extractedwith methylene chloride, the organic phase was dried over anhydrous sodiumsulfate, filtered, The solvent was evaporated to dryness, purified by silicagel column chromatography to give (trimethylsilyl)-N'-(5-cyclopropylpyridin-2-yl)prop-2-ynehydrazide (yellow solid, 0.1 1g).

Reference： [1]Current Patent Assignee: SHANGHAI PHARMACEUTICALS HOLDING COMPANY LIMITED - CN103420977, 2016, B Location in patent: Paragraph 0229-0230; 0235-0236

50
[ 4930-98-7 ]
[ 5683-30-7 ]
N'-(pyridin-2-yl)-3-(trimethylsilyl)prop-2-ynehydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 3-trimethylsilylpropionic acid With 4-methyl-morpholine; isopropyl chloroformate In ethyl acetate; toluene for 2h; Cooling with ice; Stage #2: pyrid-2-ylhydrazine In tetrahydrofuran for 1h;	1.1 The first step: (trimethylsilyl)-N'-pyridin-2-ylprop-2-ynehydrazide N-methylmorpholine (0.27 mL, 2.5 mmol ) slowly added to trimethylsilyl propionic acid (0.39 g, 2.75 mmol) in ethyl acetate (20ML) the solution is cooled in an ice bath, and then to the above solution was slowly added dropwise isopropyl chloroformate (2.0 m solution in toluene, 1.25 mL, 2.5 mmol ) after the dropwise addition, stirring was continued for 2 hours. After the reaction was completed, the reaction solution was added ice water (20ML) the quenching reaction, separating the organic phase and the organic phase washed with saturated sodium bicarbonate solution, water and saturated brine, and dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to give a yellow oil (mixed anhydride) the oil was dissolved in anhydrous tetrahydrofuran. (30ML), was added 2-hydrazinopyridine (0.24 g, 2.25 mmol), stirring was continued for 1 hour. Concentrated under reduced pressure to remove the solvent, the residue was directly used for separating and purifying by silica gel column chromatography to obtain trimethylsilyl propyne acyl -n′-pyridyl-2-hydrazide (yellow solid, 0.58)

Reference： [1]Current Patent Assignee: SHANGHAI PHARMACEUTICALS HOLDING COMPANY LIMITED - CN103420977, 2016, B Location in patent: Paragraph 0200-0203

51
[ 5683-30-7 ]
[ 119906-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / tetrahydrofuran / 2 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / -75 - 20 °C 3.1: 2,4,6-Triisopropylbenzenesulfonyl azide; potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -70 - -66 °C 3.2: -66 - 25 °C 4.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 1.83 h / 0 °C 5.1: hydrogen / palladium 10% on activated carbon / methanol / 1 h / 2482.38 Torr

Reference： [1]Current Patent Assignee: QUEST DIAGNOSTICS INC - WO2005/74904, 2005, A2

52
[ 630-18-2 ]
[ 5683-30-7 ]
[ 13169-00-1 ]
(E)-N-(4-methoxy-2,2-dimethyl-5-oxohex-3-en-3-yl)-3-(trimethylsilyl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: Methoxyallene With n-butyllithium In diethyl ether; hexane at -50℃; for 0.5h; Stage #2: tert-butyl isocyanide In diethyl ether; hexane at -78℃; for 4h; Stage #3: 3-trimethylsilylpropionic acid In diethyl ether; hexane at -78 - 20℃;	(E)-N-(4-Methoxy-2,2-dimethyl-5-oxohex-3-en-3-yl)-3-(trimethylsilyl)propanamide (3d) To a solution of methoxyallene (0.315 g, 0.34 mL, 4.50 mmol) in dry Et2O (5 mL) was added n-BuLi (1.5 mL, 3.75 mmol, 2.5 M in hexanes) at -50 °C. After 30 min stirring at -50 °C, the reaction mixture was cooled to -78 °C and trimethylacetonitrile (0.208 g, 0.27 mL, 2.50 mmol) in dry Et2O (2 mL) was added to the reaction mixture. After stirring for 4 h at the same temperature, a solution of 3-(trimethylsilyl)propionic acid (1.16 g, 7.90 mmol) in dry Et2O (3 mL) was added to the reaction mixture. The temperature was allowed to increase up to room temperature and the reaction mixture was stirred overnight. The reaction was quenched with sat. aq. NaHCO3 (20 mL) solution and the product was extracted with Et2O (3 × 25 mL). The combined organic layers were washed with brine (20 mL) and finally dried with Na2SO4. Solvent was removed in a rotary evaporator and the crude product was purified by column chromatography (SiO2, hexanes/EtOAc = 4:1) to obtain enamide 3d as pale yellow oil (0.273 g, 40%). IR (ATR): 3250 (N-H), 2990-2840 (=C-H, C-H), 1680 cm-1 (C=O). 1H NMR (CDCl3, 500 MHz): δ = -0.02 (s, 9 H, SiMe3), 0.75-0.83 (m, 2 H, CH2Si), 1.22 (s, 9 H, tBu), 2.11-2.15 (m, 2 H, CH2), 2.25 (s, 3 H, Me), 3.48 (s, 3 H, OMe), 7.00 (br s, 1 H, NH). 13C NMR (CDCl3, 125.8 MHz): δ = -2.00 (q, SiMe3), 11.2, 11.5 (2 t, SiCH2CH2), 27.5 (q, Me), 28.4, 36.5 (q, s, tBu), 58.9 (q, OMe), 133.4, 150.4 (2 s, C=C), 178.5 (s, CON), 200.8 (s, C=O). HRMS (ESI-ToF): m/z calcd for C15H29NNaO3Si [M + Na]+ 322.1809; found: 322.1821.

Reference： [1]Schefzig, Luise; Kurzawa, Timon; Rancan, Giaime; Linder, Igor; Leisering, Stefan; Bera, Mrinal K.; Gart, Max; Zimmer, Reinhold; Reissig, Hans-Ulrich [Synthesis, 2021, vol. 53, # 12, p. 2067 - 2080]

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CAS No. :	5683-30-7	MDL No. :	MFCD00002761
Formula :	C₆H₁₄O₂Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NONFLFDSOSZQHR-UHFFFAOYSA-N
M.W :	146.25	Pubchem ID :	79764
Synonyms :

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:

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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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Physical hazards
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H200	Unstable explosive
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H242	Heating may cause a fire
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H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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H301	Toxic if swallowed
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H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H335	May cause respiratory irritation
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H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361d	Suspected of damaging the unborn child
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 5683-30-7 ] {[proInfo.proName]}

Quality Control of [ 5683-30-7 ]

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[ 5683-30-7 ] Synthesis Path-Downstream 1~52

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