Acetonitrile → HCID 21392664, compound

Participants

Reaction Steps

In this preparation 10 ml. of acetonitrile is stirred in 300 ml. of anhydrous tetrahydrofuran, under nitrogen, and cooled to -70° C. 62.5 Ml. (0.1 mole) of 1.6 M butyllithium, in hexane, is added dropwise at a controlled rate such that the temperature of the mixture does not exceed -50° C. The mixture is then stirred for 5 minutes and 0.1 mole of bicyclo[3.1.0]hexan-2-one (J. Org. Chem., v. 22, 1146 (1957)) in 60 ml. of anhydrous tetrahydrofuran is added dropwise and the mixture then allowed to warm to room temperature. The mixture is then evaporated, under vacuum, to remove the tetrahydrofuran solvent and then 300 ml. of ethyl acetate is added and the mixture washed twice with water. The organic layer is dried with anhydrous magnesium sulfate and filtered. The filtrate is evaporated to dryness, under vacuum, affording 2-hydroxy-2-(bicyclo[3.1.0]hex-2-yl)acetonitrile.

Provenance & Evidence