Water → HCID 22841818, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7.3 g (20.7 mmole) of [R-(R*,S*)]-3-[4-[(tetrahydro-2H-pyran-2yl)oxy]butyl]-2-methyl-2-cyclohexene-1-propanol acetate in 68 ml of absolute ethanol was added 530 mg (2.1 mmole) of pyridinium p-toluenesulfonate and the homogeneous solution heated at 50° C. for 4 hours. The cooled reaction mixture was poured into 280 ml of water and extracted with 3×350 ml of ether. The combined organic extracts were washed with NaHCO3, brine, dried over MgSO4, filtered and concentrated. The crude product was chromatographed on a silica gel column (5:1, hexane/EtOAc) to give 4.3 g (78%) of (R)-3-[3-(acetyloxy)propyl]-2-methyl-1-cyclohexene-1-butanol as an oil.

Provenance & Evidence