Epichlorohydrin → HCID 86622515, compound

Participants

Reaction Steps

A solution of 3-(4-hydroxy-2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (600 mg, 1.68 mmol, Intermediate 20) in isopropanol (10 mL) and 3 N aq. NaOH (6 mL) is treated with epichlorohydrine (631 mg, 5.05 mmol). The reaction mixture is stirred at rt for 9 h before it is diluted with diethyl ether (150 mL) and washed with sat. aq. NaHCO3 followed by water. The organic layer is dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 3-(2-methoxy-4-oxiranylmethoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (459 mg) as an almost colourless oil; LC-MS: tR=1.13 min, [M+1]+=413.28.

Provenance & Evidence