Hydrogen Cyanide → HCID 54189769, compound

Participants

Reaction Conditions

Reaction Steps

10 mmol of pinacolone (1.25 g) were dissolved in 30 ml of methyl t-butyl ether, treated with 5 ml of enzyme solution (1000 IU/ml) and cooled to 0-5° C. with stirring. Parallel to this, 20 mmol of potassium cyanide were dissolved in 250 ml of 0.1 M aqueous citric acid with ice-cooling. The hydrocyanic acid solution prepared in this way was added to the reaction mixture and the reaction vessel was sealed pressure-tight. After a reaction time of 2.5 h, the mixture was diluted with 50 ml of methyl t-butyl ether and the reaction solution was extracted. The aqueous phase was separated off, extracted by shaking again with 80 ml of methyl t-butyl ether and then discarded. The combined organic phases were dried using anhydrous sodium sulfate and the solvent was removed under reduced pressure. After column chromatography, 0.95 g of (S)-2-hydroxy-2,3,3-trimethylbutanenitrile (75%) was obtained as a white solid (m.p. 98-99° C.).

Provenance & Evidence