反应 #2348122

反应方程式

NaOH

Thiophenol

trans-stilbene

NMP

K2CO3

→

5-[(E)-2-(4-hydroxyphenyl)-vinyl]-pyridin-2-ol

收率 69.0%

反应条件

后处理

1. 1
   其他The cooled reaction mixture
2. 2
   萃取the neutral components were extracted with ether (3×50 mL)
3. 3
   萃取extracted with ether (2×50 mL)
4. 4
   其他The solid was isolated by filtration
5. 5
   洗涤washed with water (100 mL), ethyl acetate (50 mL) and ether (30 mL)
6. 6
   其他air-dried

实验过程

The trans-stilbene (1.17 g, 4.85 mmol) was dissolved in dry NMP (12 mL). Thiophenol (1.07 g, 9.7 mmol) was then added to the above solution, followed by addition of K2CO3 (67 mg, 0.48 mmol). The resulting mixture was heated for 8 hours at 195° C. under nitrogen. The cooled reaction mixture was made alkaline with 1 N NaOH (pH=10), and the neutral components were extracted with ether (3×50 mL). The aqueous layer was acidified to pH=4 with 1 N HCl and stirred at room temperature for 30 minutes, and extracted with ether (2×50 mL). Then pH was adjusted to pH=8 with saturated NaHCO3. The solid was isolated by filtration, washed with water (100 mL), ethyl acetate (50 mL) and ether (30 mL), and air-dried to yield 5-[(E)-2-(4-hydroxyphenyl)-vinyl]-pyridin-2-ol (715 mg, 69%). MS (ES) m/z: 214.08 (M+1); 13C-NMR (DMSO-d6): δ 162.42, 157.50, 138.21, 134.07, 129.04, 127.92, 125.67, 121.59, 121.03, 116.89, and 116.18.

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