4-Bromobutyronitrile → HCID 20275170, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the 2-(3-thienyl)-2-trimethylsilyloxyacetonitrile thus obtained (14.0 g.) in tetrahydrofuran (12 ml.) was added to a stirred solution of lithium diisopropylamide [prepared at 0° C. in tetrahydrofuran solution (200 ml.) from diisopropylamine (6.7 g.) and n-butyl-lithium (43.4 ml. of 1.55 molar solution in hexane)] in tetrahydrofuran (200 ml.) which was cooled to -78° C. under an atmosphere of nitrogen, and the mixture was stirred at that temperature for 15 minutes. 4-Bromobutyronitrile (9.8 g.) was added and the mixture was stirred at -78° C. for 1 hour and then at laboratory temperature for 1 hour. Aqueous N-hydrochloric acid (75 ml.) was added, the mixture was stirred at laboratory temperature for 90 minutes and the phases were then separated. The aqueous phase was extracted twice with ethyl acetate (100 ml. each time) and the combined organic phase and extract were stirred with aqueous N-sodium hydroxide solution (50 ml.) for 18 hours. The organic phase was separated, dried and evaporated to dryness and the residue was flash chromatographed on a silica gel column using a 19:1 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil 4-cyano-1-(3-thienyl)butan-1-one.

Provenance & Evidence