1-Chloroethyl benzoate → Benzoyloxyethyl (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

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Reaction Steps

Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoic acid (12) (3.0 g, 7.9 mmol) dissolved in 30 mL of anhydrous toluene was reacted with 4.4 g (23.7 mmol) of 1-chloroethyl benzoate (23) in the presence of 2.6 g (9.5 mmol) of silver carbonate (Ag2CO3). After work-up, the crude material was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:2) as eluent to provide 3.2 g of a mixture of the title compound (39a) and (3R/S)-4,4-dimethyl-3-(phenylmethoxy)-3,4,5-trihydrofuran-2-one (2a). MS (ESI) m/z 548.97 (M+Na)+.

Provenance & Evidence