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

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%.

1. additiondropwise adding to the reaction solution
2. stirringstirring it at room temperature for 3 hours
3. extractionextracting the resulting product with ethyl acetate
4. washwashing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water
5. dry with materialdrying over magnesium sulfate
6. distillationdistilling off the solvent
7. custompurifying the resulting yellow solution
8. distillationon silica gel, and distilling the purified substance under reduced pressure by means of Vigoureux tube

ORD record

ord-9506726dbacf4f91b1c3ffaf942acc00

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05702641