Dimethyl Sulfoxide → (2-Ethoxycarbonyl)-(1-formyl)ethylene oxide

Participants

Reaction Steps

The procedure described by Evans and Williams European Patent Application No. 89302778.9, Publication No. 0334593 was employed for the Swern oxidation of (2-ethoxycarbonyl)-(1-hydroxymethyl) ethylene oxide (5.00 g) in methylene chloride (total 170 ml) with dimethylsulfoxide (7.3 mL), oxalyl chloride (4.2 mL) and triethylamine. Extractive work-up involving brine (150 mL), followed by trituration of impurities with pentane-ethyl acetate (2: 1, 450 mL ) afforded the title aldehyde (4.0 g, 80%). This material is used immediately and/or stored in dry methylene chloride at -25° C. under nitrogen.

Provenance & Evidence