反应 #355778

反应方程式

sodium bicarbonate

DMF

1-ethyl-1H-1,2,4-triazole

N,N,N′,N′-tetramethylethylenediamine

n-butyllithium

→

title compound

1-Ethyl-1H-1,2,4-triazole-5-carbaldehyde

溶剂

—

hexanes

THF

反应条件

后处理

1. 1
   workup.STIRRINGstirred for 14 hours
2. 2
   萃取The mixture was extracted with dichloromethane (3×150 mL)
3. 3
   干燥the combined organics dried over sodium sulfate
4. 4
   过滤filtered
5. 5
   浓缩concentrated

实验过程

To a solution of 1-ethyl-1H-1,2,4-triazole (9.9 g, 0.10 mol) and N,N,N′,N′-tetramethylethylenediamine (15 mL) in THF (60 mL) at −78° C. was added n-butyllithium (64 mL of a 1.6M solution in hexanes, 0.10 mol). After stirring for 2 hours, DMF (8.7 mL, 0.11 mol) was added, the reaction allowed to warm to room temperature and stirred for 14 hours before being poured into saturated aqueous sodium bicarbonate solution (300 mL). The mixture was extracted with dichloromethane (3×150 mL) and the combined organics dried over sodium sulfate, filtered and concentrated to give the title compound (>12 g) which also contained unreacted starting material 1H-NMR (CDCl3) δ 1.48 (3H, t, J=7 Hz), 4.63 (2H, q, 7 Hz), 8.03 (1H, s), 10.04 (s, 1H).

来源