Synthetic applications of 2‐chlorotetrahydrofuran: Protection of alcohols as tetrahydro‐2‐furanyl (THF) ethers
- 1 January 1979
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 98 (6) , 371-380
- https://doi.org/10.1002/recl.19790980602
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 N1‐ and N3‐monosubstituted and N1,N3‐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.Keywords
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