Valeronitrile → HCID 58380857, compound

Participants

Reaction Steps

LDA (276 mL, 553 mmol 2M in THF) was added dropwise at −78° C. under argon to a stirred solution of valeronitrile (20 g, 25.3 mL, 241 mmol) in THF (250 mL) and then stirred for 15 minutes. The reaction mixture was then warmed to room temperature and stirred for a further 20 minutes. After cooling to −78° C., cis-1,4-dichlorobutene (30.1 g, 25.3 mL) was added dropwise over 10 minutes and the mixture stirred for 10 minutes. The mixture was allowed to warm to room temperature and was then stirred overnight. The reaction was quenched by gentle addition to 150 mL ice cold water and followed by extraction with methyl tea butyl ether. Evaporation gave 47.5 g of an orange oil. Vacuum distillation 0.2-16 mbar, 55-105° C. gave 2.3 g of a yellow oil which was used without further purification.

Provenance & Evidence