Water → HCID 57306106, compound

Participants

Reaction Steps

A mixture of (E) methyl 12-(2,4-dichlorophenyl)-3-methoxycarbonyl-3-dodecenoate (1.50 g, 3.61 mmol), osmium tetroxide (0.229 ml of a 2% solution in t-butanol, 0.018 mmol), N-methylmorpholine-N-oxide (634 mg, 5.42 mmol), water (2 ml), and acetone (2 ml) was stirred at room temperature for 64 h. Aqueous NaHSO3 (1.1M, 6 ml) was added, and the mixture filtered, after 20 min, through a plug of silica gel. The silica gel plug was washed with ether, then the filtrate washed with aqueous HCl, water, and saturated aqueous NaCl. After drying (MgSO4), the solvent was removed under vacuum, and the residue purified by chromatography on silica gel (50-100% ether/petroleum ether 40°-60° C.) to give the title compound (1.33 g), contaminated with the 5-ring lactone.

Provenance & Evidence