Tetrahydrofuran → 1-Trifluoromethyl-4-(2-methoxyvinyl)benzene

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Reaction Steps

THF (1 l) was added to methoxymethyltriphenylphosphine chloride (128 g, 370 mmol), followed by adding to the mixture, potassium-t-butoxide (41.5 g, 370 mmol) at 0° C., stirring the mixture at the same temperature for 3 hours, dropwise adding to the reaction solution, a 500 ml THF solution of commercially available 4-trifluoromethylbenzaldehyde (50.0 g, 287 mmol), stirring the mixture at the same temperature for one hour, stirring it at room temperature for 3 hours, adding water (1.5 l) to the reaction solution, extracting the resulting product with ethyl acetate, washing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water, drying over magnesium sulfate, distilling off the solvent, purifying the resulting yellow solution according to column chromatography treatment using heptane/ethyl acetate (3:2) as a developing solvent, on silica gel, and distilling the purified substance under reduced pressure by means of Vigoureux tube, to obtain 1-trifluoromethyl-4-(2-methoxyvinyl)benzene (19.5 g, 96.5 mmol) (b.p. 93.5° C. under 9 Torr). Yield: 33.6%.

Provenance & Evidence