反应详情

温度

-30 °C

Into a 2 liter three-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a nitrogen gas tube, 133.7 g (390 mmol) of methoxymethyltriphenyl phosphonium chloride were charged in a nitrogen atmosphere and dried, and 450 ml of THF were added. The mixture was cooled to −30° C., 43.76 g (390 mmol) of potassium-t-butoxide were added and the mixture was stirred for 1 hr. To the mixture, a solution of 42.63 g (300 mmol) of 3,4-difluorobenzaldehyde in 150 ml of THF was added dropwise over a period of one and a half hours. The mixture was stirred as such over night and raised to room temperature. Water and heptane were added, the precipitate was filtered through Celite, and an organic layer and an aqueous layer were separated. The aqueous layer was extracted with heptane, an extract combined with the organic layer was washed with water, and the organic layer was dried over anhydrous magnesium sulfate. A solvent was distilled away from the solution, and the solution was condensed. The concentrate was purified by column chromatography (elution solvent: mixed solvent of toluene and heptane), the eluate was further purified by vacuum distillation to obtain 46.70 g of the title compound (91%, bp 98-100° C./15 Torr., cis:trans=1:1) as oily product.

1. customInto a 2 liter three-necked flask equipped with a stirrer
2. customdried
3. addition450 ml of THF were added
4. stirringThe mixture was stirred as such over night
5. temperatureraised to room temperature
6. filtrationthe precipitate was filtered through Celite
7. customan organic layer and an aqueous layer were separated
8. extractionThe aqueous layer was extracted with heptane
9. washwas washed with water
10. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
11. distillationA solvent was distilled away from the solution
12. customcondensed
13. customThe concentrate was purified by column chromatography (elution solvent: mixed solvent of toluene and heptane)
14. distillationthe eluate was further purified by vacuum distillation