Hydrochloric Acid → HCID 15389073, compound

Participants

Reaction Steps

760 mg (2.2 mmol) of methyl 2-hydroxy-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate and 20 ml of toluene are introduced into a three-necked flask under a stream of nitrogen. 4.4 ml of diisobutylaluminium hydride (1 M in toluene) are added at −78° C. and the mixture is allowed to return to room temperature. 9 ml of methanol and then 9 ml of hydrochloric acid (1 N) are successively introduced. The reaction medium is poured into an ethyl acetate/water mixture and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and then evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of ethyl acetate and heptane (50/50% by volume). After evaporation of the solvents, 200 mg (30%) of the expected alcohol are collected, with a melting point of 94-5° C.

Provenance & Evidence