Reactions of Ketones with Sodium Hydride or Potassium Hydride in the Presence of Trimethylsilyl Chloride. Preparation of Trimethylsilyl Enol Ethers

Paul F. Hudrlik, James M. Takacs

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17 Citations (Scopus)

Abstract

Reactions of cyclohexanone with NaH and Me3SiCl in various solvents yielded predominantly (90-97%) the silyl enol ether 2 resulting from enolization, with only a few percent of the alkyl silyl ether 1 resulting from initial reduction. Similar reactions with KH and Me3SiCl proceeded well only in dioxane to give >99% of 2. Cyclohexanone, 2-methylcyclohexanone, acetophenone, 2-heptanone were converted to trimethylsilyl enol ethers in good yields by this method.

Original languageEnglish (US)
Pages (from-to)3861-3865
Number of pages5
JournalJournal of Organic Chemistry
Volume43
Issue number20
DOIs
StatePublished - Jan 1 1978

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Ethers
Ketones
Hydrides
Ether
Potassium
sodium hydride
trimethylsilyl chloride
cyclohexanone
2-heptanone
1,4-dioxane
acetophenone
2-methylcyclohexanone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "Reactions of cyclohexanone with NaH and Me3SiCl in various solvents yielded predominantly (90-97{\%}) the silyl enol ether 2 resulting from enolization, with only a few percent of the alkyl silyl ether 1 resulting from initial reduction. Similar reactions with KH and Me3SiCl proceeded well only in dioxane to give >99{\%} of 2. Cyclohexanone, 2-methylcyclohexanone, acetophenone, 2-heptanone were converted to trimethylsilyl enol ethers in good yields by this method.",
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AU - Takacs, James M.

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AB - Reactions of cyclohexanone with NaH and Me3SiCl in various solvents yielded predominantly (90-97%) the silyl enol ether 2 resulting from enolization, with only a few percent of the alkyl silyl ether 1 resulting from initial reduction. Similar reactions with KH and Me3SiCl proceeded well only in dioxane to give >99% of 2. Cyclohexanone, 2-methylcyclohexanone, acetophenone, 2-heptanone were converted to trimethylsilyl enol ethers in good yields by this method.

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