A facile phase transfer catalyzed-michael addition of ethyl α (P-tolylsulfonyl)acetate to α(P-tolylsulfonyl)acetate to α,β-unsaturated esters

Abstract

The facile solid-liq. phase transfer catalyzed-Michael addition of Et a-(p-tolylsulfonyl)acetate (I) to a, b-unsatd. esters is reported. Effects of the catalyst, the Michael receptor and solvent on the conjugate addition are briefly discussed. The sulfur-contg. carbanion was generated from I with potassium carbonate under PTC conditions and then allowed to react in situ with the a,b-unsatd. esters at the temps. of 30-40癈. The Michael addition of the carbanion to acrylates, a-alkylacrylates, itaconates, crotonate, and maleate proceeded smoothly. Eight substituted pentanedioic acid esters, such as 1-ethyl-5-butyl-2-(p-tolylsulfonyl)glutarate, and two substituted hexanedioic acid esters, such as di-Et 2-(p-tolylsulfonyl)-4-ethoxycarbonyladipate, have been synthesized in good to excellent yields. The present procedure provides a mild and convenient method for the synthesis of a various substituted hexanedioic acid esters and pentanedioic acid esters. Some of the a-arylsulfonylglutarates might serve as the intermediates for preparing substituted glutaconates which are synthetically useful, and usually difficult to obtain.

Key words: ELEMENTAL ANALYSIS, INFRARED SPECTROPHOTOMETRY, POTASSIUM CARBONATE, ADDITION REACTION, P-METHYLBENZENESULFONIC ACID P, PROTON MAGNETIC RESONANCE SPECTROMETRY, PHASE TRANSFER CATALYSIS, DIETHYL ESTER, PENTANEDIOIC ACID P, P-METHYLBENZENESULFONIC ACID P

CLC Number:

O643
O651

Cite this article

ZHANG ZHENG;LIU GUANGJIAN;WANG YULIANG;XU CONGYING;HU LIANGBIN. A facile phase transfer catalyzed-michael addition of ethyl α (P-tolylsulfonyl)acetate to α(P-tolylsulfonyl)acetate to α,β-unsaturated esters[J]. Chin. J. Org. Chem., 1990, 10(5): 422-426.

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