Hydrochloric Acid → 4-Trimethylsilyl-3-cyanobutanoic acid

A solution of ethyl 4-(trimethylsilyl)-3-cyanobutanoate (341 mg, 1.60 mmol) in methanol/1,2-dimethoxyethane/water (3:2:1, 4.2 ml) was added with lithium hydroxide monohydrate (135 mg, 3.21 mmol), and the mixture was refluxed by heating for 1 hour with stirring. The reaction mixture was cooled on ice, and added with aqueous hydrochloric acid (1 N), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crystals were purified by recrystallization, and the mother solution was subjected to purification by silica gel chromatography (2% methanol/chloroform) to obtain 4-trimethylsilyl-3-cyanobutanoic acid (295 mg, quant.) mentioned in the title as colorless scaly crystals.

1. temperaturethe mixture was refluxed
2. temperatureby heating for 1 hour
3. temperatureThe reaction mixture was cooled on ice
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was evaporated
8. customThe obtained crystals were purified by recrystallization
9. customthe mother solution was subjected to purification by silica gel chromatography (2% methanol/chloroform)

ORD record

ord-a7a9f8929a98436d842cc4977abb4bd5

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895769B2