P-Toluenesulfonylhydrazide → 1,2-Di-(methoxycarbonyl)-4-ethylidene-cyclohexane

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Reaction Steps

17 g of dimethyl 1,2,3,6-tetrahydro-4-acetyl-phthalate, prepared as described in Example 1, was refluxed in anhydrous ethanol with 14.6 g of tosylhydrazine. After removal of the solvent, 24 g of dimethyl 1,2,3,6-tetrahydro-4-(1-tosylhydrazono-ethyl)-phthalate (IV) crystallized from water: m.p. 162°-163° C. m/z 408 (M+.). This compound was dissolved in chloroform, and treated at 0° C. with 14 ml of catechol borane. Sodium acetate was added to the reaction mixture, which was then refluxed. After washing with water, the solvent was evaporated off and the residue was purified by chromatography on a column of silica gel giving 10 g of the title compound (yield 80%): m/z 226 (M+.); PMR (CDCl3): inter alia δ 1.6 (d, J=8 Hz, CH3 --CH=), 5.3 (q, J=8 Hz, CH3 --CH=).

Provenance & Evidence