Epichlorohydrin → HCID 86622513, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-chloro-4-hydroxy-5-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (550 mg, 1.41 mmol, Intermediate 14) in isopropanol (10 mL) and 3 N aq. NaOH (4 mL) is treated with epichlorohydrine (0.88 g, 7.04 mmol). The dark red reaction mixture is stirred at 60° C. for 1 h. The mixture 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-(3-chloro-5-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 (400 mg) as a pale yellow oil; LC-MS: tR=1.14 min, [M+1]+=447.21; 1H NMR (CDCl3): δ 6.85-6.81 (m, 1H), 6.71-6.67 (m, 1H), 4.13 (dd, J=4.1, 11.1 Hz, 1H), 4.01 (dd, J=5.9, 11.1 Hz, 1H), 3.83 (s, 3H), 3.44-3.36 (m, 1H), 3.08-2.75 (m, 8H), 2.37 (s, 3H), 1.92-1.86 (m, 2H), 1.11 (s, 3H), 0.70 (s, 3H).

Provenance & Evidence