反応 #9004

反応方程式

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

triethylamine

acetic anhydride

→

monoacetate

2-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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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