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Silyl enol ethers as new protecting groups for alkyl 4-halo-3-oxobutanoates; The preparation of pure (3-alkoxycarbonyl-2-oxopropyl)triphenylphosphonium salts

journal contribution
posted on 2023-05-16, 10:54 authored by Moorhoff, CM
A new method has been developed for the preparation of pure (3-alkoxycarbonyl-2-oxopropyl)triphenyl-phosphonium salts 8. Alkyl 4-bromo-3-oxobutanoates and alkyl 4-chloro-3-oxobutanoates 7 are protected as the trimethylsilyl enol ethers prior to treatment of the resulting bromo(trimethylsilyl enol ether) esters 20c and 21c with triphenylphosphine in toluene and then addition of a little water to give pure (3-isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide 8c. Bromo(silyl enol ether) esters react more efficiently with triphenylphosphine than the chloro(silyl enol ether) esters. tert-Butyldimethylsilyl enol ethers of alkyl 4-bromo-3-oxobutanoates and alkyl 4-chloro-3-oxobutanoates 7 also react with triphenylphosphine. Protection of isopropyl 4-bromo-3-oxobutanoate 7c as the enol acetate followed by subsequent reaction with triphenylphosphine gives (Z)-(2-acetoxy-3-isopropoxycarbonylbut-2-enyl)triphenylphosphonium bromide 17.

History

Publication title

Journal of the Chemical Society-Perkin Transactions

Issue

13

Pagination

1987-1995

ISSN

0300-922X

Department/School

School of Natural Sciences

Publisher

The Royal Society of Chemistry

Place of publication

United Kingdom

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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