反应详情

Methyl 4-(benzylthio)-5-nitrothiophene-3-carboxylate (5 g, 16.2 mmol) in dichloromethane (150 mL) at −40° C. was reacted with diisobutylaluminum hydride (1 M in dichloromethane, 36 mL, 2.2 equivalents) added dropwise. The reaction was stirred for 15 minutes after complete addition, quenched with 10% aqueous sodium potassium tartrate solution and stirred at 25° C. for 1 hour. The organic layer was separated, filtered through Celite® (diatomaceous earth) and the filtrate was concentrated under reduced pressure. The resulting oil was purified by flash chromatography on silica gel with a Biotage-40s column eluting with 2:98 methanol/dichloromethane to give [4-(benzylthio)-5-nitrothien-3-yl]methanol as an oil, (4.32 g, 95%). 1H NMR (300 MHz, CDCl3) ppm 4.21 (s, 2 H), 4.39 (s, 2 H), 7.11 (m, 3 H), 7.23 (m, 2 H) 7.40 (s, 1 H).

1. additionadded dropwise
2. additionafter complete addition
3. customquenched with 10% aqueous sodium potassium tartrate solution
4. stirringstirred at 25° C. for 1 hour
5. customThe organic layer was separated
6. filtrationfiltered through Celite® (diatomaceous earth)
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe resulting oil was purified by flash chromatography on silica gel with a Biotage-40s column
9. washeluting with 2:98 methanol/dichloromethane