反应详情

温度

70 °C

Into a dried 5L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping fimnel, thermometer and nitrogen outlet is added 70.2 g of 60% sodium hydride (1.76 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and the mixture is heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture through the dropping funnel while keeping it at 25-30° C. The mixture is stirred for 30 minutes at room temperature at which time 2-undecanone (187 g, 1.1 mol) is slowly added through a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. The mixture is stirred for 18 hr. and then poured into a 5L beaker containing 1L purified water with stirring. The oil phase (top) is allowed to separate out in a separatory funnel and the water phase is removed. The water phase is washed with hexanes (500 ml) and the organic phase is separated and combined with the oil phase from the water wash. The organic mixture is then extracted with water 3 times (500 ml each) followed by vacuum distillation to collect the clear, oily product (132 g) at 140C and 1 mm Hg.

1. dry with materialInto a dried 5L, 3 neck round bottom flask
2. customfitted with mechanical stirring, nitrogen inlet
3. customThe mineral oil is removed
4. washby washing with hexanes
5. additionAnhydrous dimethyl sulfoxide (500 ml) is added to the flask
6. temperatureThe reaction mixture is cooled to room temperature
7. additionfollowed by addition of 1L of anhydrous tetrahydrofuran
8. additionslowly added to the reaction mixture through the dropping funnel
9. customat 25-30° C
10. additionis slowly added through a dropping funnel
11. customReaction
12. temperaturecooling
13. temperatureto maintain 25-30° C
14. custompurified water
15. stirringwith stirring
16. customto separate out in a separatory funnel
17. customthe water phase is removed
18. washThe water phase is washed with hexanes (500 ml)
19. customthe organic phase is separated
20. washwash
21. extractionThe organic mixture is then extracted with water 3 times (500 ml each)
22. distillationfollowed by vacuum distillation
23. customto collect the clear, oily product (132 g) at 140C and 1 mm Hg