反应 #1552619

反应方程式

triphenylphosphine

carbon tetrabromide

tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate

sodium hydrogen carbonate

→

tert-butyl 4-[4-(2,2-dibromovinyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

收率 97.6%

溶剂

dichloromethane

dichloromethane

dichloromethane

triethylamine

反应条件

后处理

1. 1
   workup.STIRRINGStirring
2. 2
   其他the supernatant of the reaction mixture was collected
3. 3
   workup.STIRRINGAfter stirring at 5-10° C. for 40 mins
4. 4
   过滤The mixture was filtered through a Celite pad
5. 5
   洗涤the insoluble material was washed with dichloromethane
6. 6
   洗涤The filtrate and washing solution
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

实验过程

To a solution of triphenylphosphine (7.08 g, 27 mmol) in anhydrous dichloromethane (11 ml) was added dropwise a solution of carbon tetrabromide (4.3 g, 13 mmol) in anhydrous dichloromethane (5 ml) at 10° C., and the mixture was stirred at the same temperature for 15 mins. Stirring was stopped, the supernatant of the reaction mixture was collected, and a solution of tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.0 g, 3.4 mmol) in anhydrous dichloromethane (11 ml) was added dropwise at 10° C. After stirring at 5-10° C. for 40 mins, triethylamine (4 ml) and saturated aqueous sodium hydrogen carbonate solution (0.5 ml) were added. The mixture was filtered through a Celite pad, and the insoluble material was washed with dichloromethane. The filtrate and washing solution were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to give tert-butyl 4-[4-(2,2-dibromovinyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (1.5 g, yield 97%) as a yellow oil.

来源