Sodium Thiosulfate → HCID 69655716, compound

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Reaction Steps

13.9 g of 1,1,1-triacetoxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one (Dess-Martin-Periodinane, cf. D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277) is added to a solution of 4.55 g of 3-(benzo[1,3]dioxol-4-yl)-cyclopropyl-2-hydroxypropionic acid ethyl ester in 205 ml of dichlormethane. After 6 hours at room temperature, the batch is added to a saturated solution of sodium thiosulfate and extracted with ether. It is washed with water, saturated bicarbonate solution and brine, dried (Na2SO4) and concentrated by evaporation. The residue is purified by column chromatography on silica gel with hexane-ethyl acetate (100: 0→80:20). 2.52 g of 3-(benzo[1,3]dioxol-4-yl)-cyclopropyl-2-oxopropionic acid ethyl ester is obtained. The latter is stirred in 84 ml of a solution of 1N sodium hydroxide solution in ethanol/water 2:1 at room temperature for 12 hours. The batch is concentrated in a vacuum, and the remaining solution is extracted with diethyl ether. The aqueous phase is acidified with 1 M hydrochloric acid and extracted with diethyl ether. After drying and concentration by evaporation, 2.2 g of 3-(benzo[1,3]dioxol-4-yl)-cyclopropyl-2-oxopropionic acid is obtained as a yellowish oil.

Provenance & Evidence