Реакция #9004

Уравнение реакции

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

triethylamine

acetic anhydride

→

monoacetate

2-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ПромывкаThe reaction was then washed with aqueous ammonium chloride
2. 2
   Другоеthe layers separated
3. 3
   ЭкстракцияThe aqueous layer was extracted twice with dichloromethane
4. 4
   СушкаThe combined organic fractions were then dried over anhydrous sodium sulfate
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеPurification by chromatography on silica gel (5% methanol in dichloromethane)

Методика

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).

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