| Identification | Back Directory | [Name]
(3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile | [CAS]
727382-14-1 | [Synonyms]
(S)-4-Chloro-3-(trimethylsilanyloxy)butyronitrile
(3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile
Butanenitrile, 4-chloro-3-[(trimethylsilyl)oxy]-, (3S)- | [Molecular Formula]
C7H14ClNOSi | [MDL Number]
MFCD30537510 | [MOL File]
727382-14-1.mol | [Molecular Weight]
191.73 |
| Chemical Properties | Back Directory | [Boiling point ]
233.8±20.0 °C(Predicted) | [density ]
1.002±0.06 g/cm3(Predicted) | [form ]
liquid | [color ]
light yellow | [InChI]
InChI=1S/C7H14ClNOSi/c1-11(2,3)10-7(6-8)4-5-9/h7H,4,6H2,1-3H3/t7-/m0/s1 | [InChIKey]
FLYSOKSACGLOAO-ZETCQYMHSA-N | [SMILES]
C(#N)C[C@H](O[Si](C)(C)C)CCl |
| Hazard Information | Back Directory | [Description]
(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile, also known as
(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile, is a useful research
compound. Its molecular formula is C7H14ClNOSi and its molecular
weight is 191.73 g/mol. The purity is usually 95%. | [Uses]
(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile is used in the synthesis of statins or HMG-CoA reductase inhibitors. | [Synthesis]
The synthesis of (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile is as follows:
To a solution of (S)-4-chloro-3-hydroxy butanenitrile (52.5 g) in THF (150 mL) was added trimethyl silyl chloride (57.2 g) under inert atmosphere at 25 °C. The resulting reaction mixture was stirred for 10 min at 20°C. A solution of triethyl amine (53.4 g) in THF (100 mL) was added to above reaction mixture by maintaining reaction temperature below 40 °C. To the resulting reaction mixture catalytic amount of sodium iodide was added and stirred further for 5 h at 40°C. Reaction was monitored on GC as well TLC for complete conversion of starting material. After cooling to 0 °C, a 21% aqueous solution of sodium chloride (500 mL) was added and extracted with ethyl acetate (2 X 300 mL). Combined organic layer was dried with anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile as light brown liquid (84.0 g, 99%).
![synthesis of (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile.png](/NewsImg/2022-12-01/6380548217412583178427824.jpg "synthesis of (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile.png") |
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