Sodium Methoxide → HCID 19806755, compound

Participants

Reaction Steps

To the solution of 3-ethoxy-4,5-dichloroisothiazole-1-oxide (0.12 g, 0.00056 mol) in methanol (1 ml) cooled in an ice-bath was added a solution of sodium methoxide (0.032 g, 0.00060 mol) methanol (1 ml). The solution was warmed to ambient temperature and stirred overnight. The solution was concentrated to dryness in vacuo and the residue was partitioned between chloroform (10 ml) and water (5 ml). The aqueous layer was washed with chloroform (10 ml) and the combined organic layers were washed with saturated sodium chlorate solution (2 ml) dried over sodium sulfate, filtered, and concentrated to dryness to give 0.14 g orange liquid. This liquid was chromatographed on a column of E. Merck silica gel 60. From the fraction eluted with n-butylchloride, there was obtained 0.06 g of a mixture of starting material and 3-methoxy-4,5-dichloroisothiazole-1-oxide. From the fractions eluted with methylene chloride, there was obtained 0.03 g (25%) of the title compound. TLC (methylene chloride silica): Rf=0.43 (identical to product of Step B above.

Provenance & Evidence