反应 #72725

反应方程式

Niacin

Vanillin

N-methyl morpholine

EDCI.HCl

→

title compound

Nicotinic acid 4-formyl-2-methoxy-phenyl ester

溶剂

water

dichloromethane

反应条件

后处理

1. 1
   萃取extracted with dichloromethane
2. 2
   干燥the organic layer dried over anhydrous sodium sulfate
3. 3
   浓缩concentrated
4. 4
   其他The crude product thus obtained
5. 5
   其他was then chromatographed

实验过程

To a solution of Niacin 1 (1.6 g, 13.1 mmol) in dichloromethane (10 mL) was added Vanillin 8 (2 g, 13.1 mmol), N-methyl morpholine (4.3 mL, 39 mmol) and EDCI.HCl (5 g, 26.2 mmol). The resulting mixture was stirred at ambient temp for 3 h. It was then diluted with water, extracted with dichloromethane, and the organic layer dried over anhydrous sodium sulfate and concentrated. The crude product thus obtained was then chromatographed using over a column of silica gel using petroleum ether:ethyl acetate (1:1) to afford the title compound as a off white solid (300 mg, 9%, mp (° C.): 92-94) 1H NMR (300 MHz, DMSO-D6): 10.02 (s, 1H), 9.25 (d, J=2 Hz, 1H), 8.93 (dd, J=5 & 1.5 Hz, 1H), 8.48 (dt, J=1.8 Hz & 8 Hz, 1H), 7.67 (m, 3H), 7.57 (d, J=8 Hz, 1H), 3.87 (s, 3H)); LCMS (m/z): 257.7 (M+1); HPLC: tRet: 6.486 (98.9%).

来源