Water → (+)-8-Chloro-6-methanesulfonyloxy-octanoic acid

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Reaction Steps

The methyl ester of (+)-8-chloro-6-hydroxy-octanoic acid (+)-(VIII) (R=Me) (4.0 g, 19.2 mmoles) and 1.97 g (19.2 mmoles) of triethylamine were mixed in 90 ml toluene. While cooling to an internal temperature of 10° to 15° C., 2.63 g (23.0 mmoles) of methanesulfonyl chloride were added slowly. Stirring was continued for 30 minutes. After the addition of 30 ml of water, stirring was continued for a further 30 minutes, after which the organic phase was removed and dried over magnesium sulfate. The solvent was then evaporated under vacuum. The methyl ester of (+)-8-chloro-6-methanesulfonyloxy-octanoic acid (+)-(II) (R=R'=Me) was obtained in a yield of 4.8 g (88% of the theoretical yield). [α]D20 =+31.2° (c=1; ethanol).

Provenance & Evidence