Diethylaminosulphur Trifluoride (DAST) as an Effective Reagent for Preparation of Methyl 2-Arylpropanoates from 1-Aryl-1,1-dimethoxypropan-2-ols

DOI: 10.1039/P19900001683

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1683 - 1685 (1990)

Update date:2022-08-10

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Authors:

Yamauchi, Takayoshi

Hattori, Kaneaki

Ikeda, Shun-ichi

Tamaki, Kentaro

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Article abstract of DOI:10.1039/P19900001683

Treatment of dimethylacetals of aryl 1-hydroxyethyl ketones (Ar= Ph, 4-PhC6H4, 4-BuⁱC6H4, 4-MeOC6H4, 4-BrC6H4, 6-MeOnaphthalen-2-yl) with diethylaminosulphur trifluoride (DAST) affords smoothly the methyl 2-arylpropanoates in good yield via aryl-group migration.On the other hand, treatment of aryl 1-hydroxyethyl ketones with DAST gives the corresponding aryl 1-fluoroethyl ketones (Ar= Ph, 4-PhC6H4, 4-BuⁱC6H4) in high yield.

Full text of DOI:10.1039/P19900001683

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