تفاعل #9004

معادلة التفاعل

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

triethylamine

acetic anhydride

→

monoacetate

2-acetoxymethyl-5-hydroxymethyl-N-benzylimidazole

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   غسيلThe reaction was then washed with aqueous ammonium chloride
2. 2
   أخرىthe layers separated
3. 3
   استخلاصThe aqueous layer was extracted twice with dichloromethane
4. 4
   تجفيفThe combined organic fractions were then dried over anhydrous sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىPurification by chromatography on silica gel (5% methanol in dichloromethane)

الإجراء التجريبي

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).

المصدر