Reaction #3077

Reaction equation

(+)-8-chloro-6-hydroxy-octanoic acid

triethylamine

water

methanesulfonyl chloride

→

(+)-8-chloro-6-methanesulfonyloxy-octanoic acid

Solvents

toluene

Conditions

Workup

1. 1
   workup.ADDITIONwere added slowly
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for a further 30 minutes
4. 4
   Otherafter which the organic phase was removed
5. 5
   Dryingdried over magnesium sulfate
6. 6
   OtherThe solvent was then evaporated under vacuum

Procedure

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).

Source