반응 #9004

반응 방정식

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

triethylamine

acetic anhydride

→

monoacetate

2-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole

용매

dichloromethane

반응 조건

후처리

1. 1
   세척The reaction was then washed with aqueous ammonium chloride
2. 2
   기타the layers separated
3. 3
   추출The aqueous layer was extracted twice with dichloromethane
4. 4
   건조The combined organic fractions were then dried over anhydrous sodium sulfate
5. 5
   농축concentrated
6. 6
   기타Purification by chromatography on silica gel (5% methanol in dichloromethane)

실험 절차

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).

출처