Ethanol → HCID 67054475, compound

Participants

Reaction Steps

Solid t-BuOK (240 mg, 2.15 mmol) was added as 6 portions to a solution of ketone 1B (300 mg, 1.07 mmol) and TosMIC (273 mg, 1.40 mmol) in a mixture of DME (5.0 mL) and absolute EtOH (1 mL) while keeping the temperature between 5 and 10° C. The reaction mixture was allowed to warm to rt and was maintained for 30 min. The reaction mixture was then heated at 35-40° C. for 30 min and was then allowed to cool to rt. The precipitate (TosK) was removed by filtration and the filter cake was washed with DME. The combined organic layers were concentrated and the residue was purified by column chromatography (0/100 to 10/90 MeOH/EtOAc) to provide nitrile 17A (203 mg, 70%) as a mixture of equatorial and axial isomers. Data: LC/MS (ESR) m/z=291 [M+H]+.

Provenance & Evidence