Hydrochloric Acid → HCID 22111430, compound

Participants

Reaction Steps

To a solution of 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclobutan-1-one (0.50 g, 1.76 mmol) (prepared in example 2b) in tetrahydrofuran (10 mL) at −30-40° C. under an argon atmosphere was added over 15 min a slurry of lithium borohydride (0.12 g, 5.28 mmol) in tetrahydrofuran (16 mL). The reaction was stirred 0.5 h and was poured into 0° C. ammonium chloride. 10% Hydrochloric acid was used to adjust to pH 3-4, the mixture was warmed to room temperature and was extracted with three portions of diethyl ether. The organic extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 2:8 ethyl acetate : hexanes provided product as a colorless oil (0.54 g, 100%). 1H-NMR indicated the cis: trans isomer ratio to be ˜85:15.

Provenance & Evidence