反応 #595301

反応方程式

2-(bromomethyl)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane

sodium hydride

2-iodoimidazole

→

1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2-iodo-1H-imidazole

収率 72.0%

溶媒

DMF

DMF

water

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting mixture was stirred at 50° C. for 20 h
2. 2
   workup.WAITat 80° C. for 3 h
3. 3
   温度After cooling to room temperature
4. 4
   抽出extracted with AcOEt
5. 5
   その他the extracts were dried
6. 6
   濃縮concentrated to dryness under reduced pressure
7. 7
   濃縮concentrated to dryness under reduced pressure
8. 8
   その他Purification of the residue on silica gel

実験手順

At 3° C., sodium hydride (60% by weight strength dispersion in mineral oil, 56.7 mg, 1.41 mmol) was added to a stirred solution of 2-iodoimidazole (242 mg, 1.25 mmol) in dry DMF (8 ml). The reaction mixture was stirred at room temperature for 20 min, and 2-(bromomethyl)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane (300 mg, 0.83 mmol) in dry DMF (4 ml) was then added. The resulting mixture was stirred at 50° C. for 20 h and then at 80° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with water and extracted with AcOEt, and the extracts were dried and concentrated to dryness under reduced pressure. The filtrates were combined and concentrated to dryness under reduced pressure. Purification of the residue on silica gel gave 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2-iodo-1H-imidazole as a 55/45 mixture of diastereoisomers [298 mg, colourless solid, yield 72%; HPLC/MS: m/z=473 (M+H); log P(HCOOH)=2.92 (major diastereoisomer), 3.31 (minor diastereoisomer)].

出典