反应详情

24.5 g (0.05 M) of 4-bromo-pent-2trans-en-1-yl triphenylphosphonium bromide [which can be prepared according to the above given procedure] were slowly added to a suspension kept under stirring and in argon atmosphere of 13.5 g (0.12 M) of potassium ter-butoxide in 100 ml of anhydrous ether. The reaction mixture was kept under stirring overnight, whereupon 5 g (0.05 M) of hexanal in 35 ml of anhydrous ether were added thereto at a temperature of ca. 15°-25°. After having been left at 35° for 1 h, the mixture was cooled to room temperature, diluted with 130 ml of hexane, filtered over Celite and the clear filtrate, after washing with a saturated aqueous solution of NH4Cl and drying over magnesium sulphate, was kept 1 day at -20°. A subsequent purification was carried out by column chromatography by using 100 g of silica gel and elution with hexane. By distillation of the residue obtained on evaporation of the volatile portion of the eluate, 2.8 g (37 %) of a mixture comprising 44:56 parts by weight of hydrocarbons Ic and Id was obtained.

1. custom24.5 g (0.05 M) of 4-bromo-pent-2trans-en-1-yl triphenylphosphonium bromide [which can be prepared
2. additionwere slowly added to a suspension
3. additionwere added
4. customat a temperature of ca. 15°-25°
5. filtrationfiltered over Celite
6. washthe clear filtrate, after washing with a saturated aqueous solution of NH4Cl
7. dry with materialdrying over magnesium sulphate
8. waitwas kept 1 day at -20°
9. customA subsequent purification
10. wash100 g of silica gel and elution with hexane
11. distillationBy distillation of the residue