Synthetic applications of 2-chlorotetrahydrofuran: Protection of alcohols as tetrahydro-2-furanyl (THF) ethers

✍ Scribed by C. G. Kruse; F. L. Jonkers; V. Dert; A. van der Gen

• Book ID: 104588133
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 1013 KB
• Volume: 98
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19790980602

✦ Synopsis

Abstract

2‐Chlorotetrahydrofuran (2‐Cl‐THF) is formed in 85% yield by reaction of sulfuryl chloride with excess THF. 2‐Cl‐THF reacts with alcohols, phenols, acids, thiols, azoles, amides and imides to give the corresponding tetrahydro‐2‐furanyl derivatives. Reaction with uracil derivatives provides N^1^‐ and N^3^‐monosubstituted and N^1^,N^3^‐disubstituted compounds. The reaction with alcohols provides a convenient general procedure for protecting the hydroxyl function. The THF group can be readily removed by acid catalyzed hydrolysis or reaction with methanol. The THF derivative of diphenylacetic acid can also be utilised for introducing the tetrahydro‐2‐furanyl moiety. THF ethers are converted into alkyl bromides by treatment with triphenylphosphine dibromide.