Dichloromethane → HCID 68146124, compound

Participants

Reaction Steps

To a slurry of 0.420 g of lithium tetrahydro-aluminate(1-) in 400 ml of ether is slowly added, with stirring, a solution of 0.780 g of (1S,2S,5S)-2-acetoxy-5-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)-1-methylcyclopentaneacetic acid in a mixture of 10 ml of diethyl ether and 5 ml of THF. When the addition is complete, stirring is continued at room temperature for 18 hours, whereupon 1.7 ml of aqueous 5% sodium hydroxide followed by 40 ml of dichloromethane is introduced. The resultant mixture is filtered. Solvent is stripped from the filtrate by vacuum distillation, leaving a white solid residue which, crystallized from a mixture of benzene and hexane, affords (1S,2S,5S)-5-(1,2,3,4-tetrahydro-6-methoxy-2-naphthyl)-2-hydroxy-1-methylcyclopentaneethanol melting at 151°-153° further characterized by a specific rotation of +62°.

Provenance & Evidence