反応 #62691

反応方程式

2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine

thionyl chloride

3-bromopropanol

→

2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine

溶媒

CH2Cl2

DMF

反応条件

後処理

1. 1
   温度cooled to 5° C
2. 2
   workup.STIRRINGthe solution stirred for 1 hour at room temperature
3. 3
   洗浄The solution was then washed with water
4. 4
   乾燥the organic layer dried over sodium sulfate
5. 5
   その他evaporated under reduced pressure
6. 6
   その他The product was recrystallized from ethyl acetate

実験手順

A solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine (107 g, 0.32 mol) in CH2Cl2 (520 mL) and DMF (100 mL) was cooled to 0° C. and thionyl chloride (28 mL, 0.39 mol) slowly added. The mixture was stirred at room temperature for 1 hour, then cooled to 5° C. Distilled 3-bromopropanol (35 mL, 3.9 mol) was slowly added, and the solution stirred for 1 hour at room temperature. The solution was then washed with water and the organic layer dried over sodium sulfate and evaporated under reduced pressure. The product was recrystallized from ethyl acetate to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine (12, mp=146° C.).

出典