A Fortuitously Straightforward Synthesis of 4-Acetoxy-2-Propyltetrahydrothiophene. (December 2015)

• Record Type: Journal Article
• Authors: Ma, Bianbian; Yang, Shaoxiang; Tao, Feiyan; Sun, Baoguo; Liu, Yongguo; Tian, Hongyu
• Is Part Of: Journal of chemical research. Volume 39:Number 12(2015)
• Page Start: 724
• Page End: 726
• Publication Date: 2015-12
• Subjects: 1-hepten-4-ol -- 1, 2-epoxy-4-heptanol -- 1, 2-epoxy-4-heptyl mesylate -- 4-acetoxy-2-propyltetrahydrothiophene -- thioacetate; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751915X14476078040135
• Languages: English
• ISSNs: 1747-5198

Abstract

4-Acetoxy-2-propyltetrahydrothiophene was synthesised from 1-hepten-4-ol by a three-step route involving epoxidation and mesylation to 1, 2-epoxy-4-heptyl mesylate and then reaction with thioacetate. An acetoxylated cyclic product was formed instead of the expected thioacetate, and a mechanism for its formation using an intramolecular transesterification is proposed.