Hydrochloric Acid → HCID 13552981, compound

Participants

Reaction Conditions

Reaction Steps

Aluminum chloride (78.0 mmol) dissolved in diethyl ether (40 mL) under nitrogen was added to a suspension of lithium aluminum hydride (78.0 mmol) in diethyl ether (40 mL) under nitrogen at 0° C. To the reaction mixture was added a solution of Compound 3a (52.0 mmol) in diethyl ether (25 mL) at such a rate that reflux was maintained. After an additional 15 minutes at reflux, the reaction mixture was cooled to 0° C. and dilute 3M sulfuric acid was added dropwise until the evolution of gas stopped. The reaction mixture was then poured onto ice (100 mL) and 3N hydrochloric acid (25 mL) and then extracted with diethyl ether (2×50 mL). The combined organic phases were washed with 3N hydrochloric acid, saturated aqueous sodium bicarbonate, water and brine and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel eluted with ethyl acetate:hexane (2:98) to afford Compound 3b as an oil (Rf =0.4).

Provenance & Evidence