反应 #9004

反应方程式

2,5-bis-(hydroxymethyl)-N-benzylimidazole

triethylamine

acetic anhydride

→

monoacetate

2-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole

溶剂

dichloromethane

反应条件

后处理

1. 1
   洗涤The reaction was then washed with aqueous ammonium chloride
2. 2
   其他the layers separated
3. 3
   萃取The aqueous layer was extracted twice with dichloromethane
4. 4
   干燥The combined organic fractions were then dried over anhydrous sodium sulfate
5. 5
   浓缩concentrated
6. 6
   其他Purification by chromatography on silica gel (5% methanol in dichloromethane)

实验过程

To a solution of 2,5-bis-(hydroxymethyl)-N-benzylimidazole (436 mg, 2.0 mmol) in dichloromethane (10 mL) was added triethylamine (0.35 mL, 2.0 mmol) and acetic anhydride (0.19 mL, 2.0 mmol). The mixture was then stirred overnight (16 h) at room temperature. The reaction was then washed with aqueous ammonium chloride and the layers separated. The aqueous layer was extracted twice with dichloromethane. The combined organic fractions were then dried over anhydrous sodium sulfate and concentrated. Purification by chromatography on silica gel (5% methanol in dichloromethane) gave the monoacetate, 2-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole, as a white powder (300 mg, 58%). 1H NMR (CDCl3) δ 1.83 (s, 3H), 4.49 (s, 2H), 5.06 (s, 2H), 5.33 (s, 2H), 6.97 (m, 2H), 7.28 (m, 3H).

来源