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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The preparation of ethyl and isopropyl dienol ethers and dienol pivalate esters from Hagemann's ester and its t-butyl analogue, and the reactions of the derived ester dienolates with electrophiles

MV Baker, C Ghitgas, RK Haynes, AE Hilliker, GJ Lynch, GV Sherwood and H Yeo

Australian Journal of Chemistry 37(10) 2037 - 2058
Published: 1984

Abstract

The preparation of ethyl 4-ethoxy-2-methylcyclohexa-1,3-diene-1-carboxyate, ethyl 4-isopropoxy- 2-methylcyclohexa-1,3-diene-1-carboxylate, t-butyl 4-isopropoxy-2-methylcyclohexa-1,3-diene-1- carboxylate, ethyl 4-(t-butylcarbonyloxy)-2-methylcyclohexa-1,3-diene-1-carboxylate, and t-butyI 4-(t-butylcarbonyloxy)-2-methylcyclohexa-1,3-diene-1-carboxylate from Hagemann's ester and its t-butyl analogue in the presence of diethyl or diisopropyl sulfates and sodium hydride in dimethyl sulfoxide, or pivaloyl chloride and N,N,N',N'-tetramethylethylenediamine in tetrahydrofuran is described. The foregoing dienol ethers and esters are smoothly deprotonated by lithium diisopropyl- amide in tetrahydrofuran at -78" to give the corresponding ester dienolates, which react regio- specifically with a number of electrophiles, either a or y to the alkoxycarbonyl group of the dienol ether or ester. A number of the products, which are generally obtained in good yields, have been hydrolysed to Hagemann's ester derivatives substituted exclusively at C1.

https://doi.org/10.1071/CH9842037

© CSIRO 1984

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