Dimethylformamide → 5-Prop-2-en-1-ylidene-10,11-dihydro-5H-dibenzo(a,d)(7)annulene

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Reaction Conditions

Reaction Steps

A mixture of 5-(3-mesyloxypropylidene)-10,11-dihydro-dibenzo[a,d]cycloheptene (5.0 g, 15.2 mmol), ethyl 3-(4-hydroxyphenyl)-2-ethoxypropionate (3.7 g, 15.5 mmol), potassium carbonate (2.9 g, 21 mmol) and dimethylformamide (10 ml) was heated at 100° C. for 5 h. Benzene (200 ml) and water (200 ml) were added and the phases separated. The organic phase was dried, the solvent evaporated, and the product purified by chromatography on silica gel (benzene/chloroform eluent) to give first 2.5 g of 5-propenylidene-10,11-dihydro-5H-dibenzo(a,d)cycloheptene and then the title compound as an oil; 1.5 g (21%).

Provenance & Evidence