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

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Reaction Steps

THF (1.8 l) was added to methoxymethyltriphenylphosphine chloride (350 g, 1.02 mol), followed by adding to the mixture, potassium-t-butoxide (114 g, 1.02 mol), stirring the mixture at the same temperature, for 3 hours, dropwise adding to the reaction solution, a 750 ml THF solution of commercially available 4-trifluoromethoxybenzaldehyde (150.0 g, 0.79 mol), stirring the mixture at the same temperature for one hour, further 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 product under reduced pressure, by means of Vigoureux tube, to obtain 1-trifluoromethoxy-4-(2-methoxyvinyl)benzene (138 g, 0.63 mol). (b.p. 91° C. under 9 Torr). Yield: 79.7%.

Provenance & Evidence