تفاعل #341724

معادلة التفاعل

1-benzyl-2-chloromethyl-1H-imidazole

1-benzyl-2-chloromethyl-1H-imidazole hydrochloride

sodium ethanolate

potassium iodide

sodium ethanolate

3,5-heptanedione

→

4-(1-benzyl-1H-imidazol-2-ylmethyl)-heptane-3,5-dione

المردود 31.5%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated to 50° C. for 10 min
2. 2
   درجة الحرارةimmediately cooled to ambient temperature
3. 3
   تركيزconcentrated under reduced pressure at max
4. 4
   أخرى30° C
5. 5
   أخرىPurification by flash-chromatography on silica gel with heptane/ethyl acetate 1:1 as eluent

الإجراء التجريبي

To a solution of 1.74 ml (4.7 mmol; ˜21% solution in ethanol) sodium ethanolate in 18 ml dry ethanol were added 600 mg (4.7 mmol) 3,5-heptanedione and stirred at ambient temperature for 30 min. Then a solution of 1-benzyl-2-chloromethyl-1H-imidazole (prepared from 1.081 g (4.5 mmol) 1-benzyl-2-chloromethyl-1H-imidazole hydrochloride in 7 ml ethanol and 1.74 ml (5 mmol; ˜21% solution in ethanol) sodium ethanolate) was added together with 30 mg potassium iodide. The mixture was heated to 50° C. for 10 min and then immediately cooled to ambient temperature and concentrated under reduced pressure at max. 30° C. Purification by flash-chromatography on silica gel with heptane/ethyl acetate 1:1 as eluent provided 423 mg 4-(1-benzyl-1H-imidazol-2-ylmethyl)-heptane-3,5-dione as light brown oil: MS (ISP): 299.2 ((M+H)+.).

المصدر