A Convenient and Practical Preparation of 4-Chloromethyl-5-methyl-1,3-dioxol-2-one

• IKEDA S.

  Pharmaceuticals Reseach Center, Kanebo Ltd.,

• TAKEBE YASUSHI

  Pharmaceuticals Reseach Center, Kanebo Ltd.,

• HIRAYAMA RYOICHI

  Pharmaceuticals Reseach Center, Kanebo Ltd.,

• SAKAMOTO FUMIO

  Pharmaceuticals Reseach Center, Kanebo Ltd.,

• IUCHI KOJI

  Pharmaceuticals Reseach Center, Kanebo Ltd.,

• TSUKAMOTO GORO

  Pharmaceuticals Reseach Center, Kanebo Ltd.,

Abstract

A new-synthetic method for 4-chloromethyl-5-methyl-1,3-dioxol-2-one (1c), which is useful for preparing prodrugs, has been developed. Ene-chlorination of 4,5-dimethyl-1,3-dioxol-2-one (2) with chlorine or sulfuryl chloride afforded 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one (3) in good yield. Compound 3 underwent allylic rearrangement to afford 1c quantiatively. The overall yield of 1c from 2 was approximately 80%.

Journal

• Chem. Pharm. Bull.

  Chem. Pharm. Bull. 36 394-397, 1988

  The Pharmaceutical Society of Japan

Keywords

• 4-chloromethyl-5-methyl-1, 3-dioxol-2-one
• 4, 5-dimethl-1, 3-dioxol-2-one
• 4-chloro-4-methyl-5-methylene-1, 3-dioxolan-2-one
• ene-chlorination
• allylic rearrangement
• (5-methyl-2-oxo-1, 3-dioxol-4-yl)methyl group
• promoiety
• prodrug

Details

• CRID: 1570009752553559680
• NII Article ID: 110003626700
• NII Book ID: AA00602100
• ISSN: 00092363
• Text Lang: en
• Data Source:
  • CiNii Articles