반응 #2455658

반응 방정식

1-(4-fluorophenyl)-2-mercapto-N-methoxy-N-methyl-1H-imidazole-5-carboxamide

lithium aluminum hydride

→

1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carbaldehyde

용매

THF

반응 조건

후처리

1. 1
   기타The reaction was quenched at 0° C. with 15% sodium bicarbonate (40 mL) and water (40 mL)
2. 2
   추출extracted with ethyl acetate
3. 3
   건조The combined organic layers were dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes)

실험 절차

To a solution of 1-(4-fluorophenyl)-2-mercapto-N-methoxy-N-methyl-1H-imidazole-5-carboxamide (8) (1 g, 3.55 mmol) in anhydrous THF (71 mL) at 0° C. was added lithium aluminum hydride (2M in THF, 5.3 mL, 10.65 mmol). The reaction was stirred at 0° C. for 1 h and for an additional 3 h at room temperature. The reaction was quenched at 0° C. with 15% sodium bicarbonate (40 mL) and water (40 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carbaldehyde (12).

출처