反应 #637123

反应方程式

ammonium chloride

potassium tert.-butoxide

(1-naphthylmethyl)triphenylphosphonium chloride

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

→

tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture is stirred at 0° C. for another 30 min
2. 2
   温度slowly warmed to room temperature
3. 3
   workup.WAITAfter a further 20 min
4. 4
   其他the aqueous phase is separated off
5. 5
   萃取After extraction of the aqueous phase with ethyl acetate
6. 6
   干燥the combined organic phases are dried over sodium sulphate
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他After chromatographic purification

实验过程

Under argon, (1-naphthylmethyl)triphenylphosphonium chloride (2.96 g) is dissolved in 20 ml of tetrahydrofuran and cooled to 0° C., and potassium tert.-butoxide (757 mg) is added, whereupon the colour of the solution changes to dark-red. After 10 min of stirring, tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (1.00 g) is added. The mixture is stirred at 0° C. for another 30 min and then slowly warmed to room temperature. After a further 20 min, saturated ammonium chloride solution is added, and the aqueous phase is separated off. After extraction of the aqueous phase with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives tert-butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.2 g, Z isomer).

来源