Carbonic acid, 1-chloroethyl ethyl ester → HCID 86628903, compound

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Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoic acid (11) (1.0 g, 2.4 mmol) dissolved in 15 mL of anhydrous toluene was reacted with 1.1 g (7.3 mmol) of commercially available 1-chloroethyl ethoxyformate in the presence of 0.81 g (2.9 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 0.77 g of a mixture of the title compound (36a) and (3R)-4,4-dimethyl-3-[(4-methoxyphenyl)methoxy]-3,4,5-trihydrofuran-2-one. MS (ESI) m/z 546.99 (M+Na)+.

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