A simple and efficient synthesis of fatty thioacids.
A rapid and high-yielding two-step synthesis of fatty thioacids from readily available starting materials has been devised. In the first step, an acid chloride is reacted with thioacetic acid at room temperature to produce a mixed thioanhydride, which in the second step is nucleophilically deacetylated with propylamine or butylamine at 5 degrees C. Each step is complete in five minutes and proceeds in quantitative yield. The versatility of the procedure is demonstrated by the synthesis of fatty thioacids from six to sixteen carbons in length.
Shin
H C
HC
Chemistry Department, University of Iowa, Iowa City 52242.
Quinn
D M
DM
D005069:Evaluation Studies as Topic; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D008722:Methods; D013055:Spectrophotometry, Infrared; D013438:Sulfhydryl Compounds
D005227:Fatty Acids; D013438:Sulfhydryl Compounds; C005732:thioacetic acid