反应 #637122

反应方程式

ammonium chloride

potassium tert-butoxide

diethyl 1-naphthylmethylphosphonate

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

→

tert-Butyl 4-{4-[(E)-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 30 min
2. 2
   温度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extracted with ethyl acetate
6. 6
   干燥The combined organic phases are dried over sodium sulphate
7. 7
   浓缩concentrated
8. 8
   其他the residue is purified chromatographically

实验过程

Under argon, diethyl 1-naphthylmethylphosphonate (1.88 g) is dissolved in tetrahydrofuran (20 ml) and cooled to 0° C. 757 mg of potassium tert-butoxide are added, whereupon the colour of the solution changes to dark-red. After a further 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 30 min and then warmed to room temperature. After a further 20 min, conc. ammonium chloride solution is added. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated, and the residue is purified chromatographically. This gives tert-butyl 4-{4-[(E)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.16 g) as the E isomer.

来源