(3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile

Base Information

• Chemical Name: (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile
• CAS No.: 727382-14-1
• Molecular Formula: C₇H₁₄ClNOSi
• Molecular Weight: 191.733
• Mol file: 727382-14-1.mol

Synonyms:(3S)-4-chloro-3-[(trimethylsilyl)oxy]butyronitrile

Chemical Property of (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile

Chemical Property:

• Boiling Point: 233.8±20.0 °C(Predicted)
• Density: 1.002±0.06 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• 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.

Technology Process of (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile

There total 4 articles about (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

chloro-trimethyl-silane (75-77-4) + (S)-4-chloro-3-hydroxy butyronitrile (127913-44-4,637-75-2) → (3S)-4-chloro-3-[(trimethylsilyl)oxy]butyronitrile (727382-14-1)

Guidance literature:

chloro-trimethyl-silane; (S)-4-chloro-3-hydroxy butyronitrile; In tetrahydrofuran; at 20 - 25 ℃; for 0.166667h; Inert atmosphere;

With triethylamine; sodium iodide; In tetrahydrofuran; at 40 ℃; for 5h; Inert atmosphere;

Reference yield:

trimethylsilyl cyanide (7677-24-9) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 4-chloro-3-((trimethylsilyl)oxy)butanenitrile (927674-56-4) + (3S)-4-chloro-3-[(trimethylsilyl)oxy]butyronitrile (727382-14-1)

Guidance literature:

epichlorohydrin; With titanium(IV) isopropylate; C₆₄H₇₈N₄O₄; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

trimethylsilyl cyanide; In dichloromethane; at 20 ℃; for 24h; Temperature; Time; Reagent/catalyst; Overall yield = 60 %; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.04.012

Reference yield:

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + (S)-4-chloro-3-hydroxy butyronitrile (127913-44-4,637-75-2) → (3S)-4-chloro-3-[(trimethylsilyl)oxy]butyronitrile (727382-14-1)

Guidance literature:

In toluene; for 4h; Solvent; Reflux;

upstream raw materials:

chloro-trimethyl-silane

(S)-4-chloro-3-hydroxy butyronitrile

trimethylsilyl cyanide

epichlorohydrin

Downstream raw materials:

Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

Refernces

• 1、 -. "Method for synthesizing ADA". Paragraph 0081; 0083; 0084; 0085; 0102. . Retrieved 2018/02/04.
• 2、 -. "A NOVEL, GREEN AND COST EFFECTIVE PROCESS FOR SYNTHESIS OF TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDENE-HEXANOATE". Page/Page column 34; 35. . Retrieved 2015/01/07.