tert-Butyl acetate → HCID 14852352, compound

Participants

Reaction Steps

n-BuLi (1.6M, 6 ml) was added over 5 min. to a stirred, cooled (-10°) solution of cyclohexylisopropylamine (1.64 ml) in dry THF (10 ml) under nitrogen. After 5 min., the solution was cooled to -78° and 15 min. later tert-butyl acetate (1.35 ml) was added over 5 min. After 20 min. cis-1,4-dichloro-2-butene (4 ml) was added and the mixture was allowed to warm to 10° over 4 h. The mixture was diluted with 1N HCl (25 ml) and extracted with ER (2×30 ml). The combined extracts were successively washed with 1N HCl (20 ml), brine (20 ml) and 8% NaHCO3 solution (20 ml) then dried and evaporated. The excess of dichloromethane was removed in vacuo and the residue was purified by chromatography (A) using PE, followed by 1:1 CH2Cl2 -PE increasing to CH2Cl2 as eluant to give the title compound as an oil (0.66 g)

Provenance & Evidence