反应详情

Under a nitrogen atmosphere 200 mL (200 mmol) of a 1M borane in THF solution were slowly added dropwise at RT to 12.6 g (65.7 mmol) (5-methoxy-2-nitrophenyl)-acetonitrile in 380 mL THF. The reaction mixture was refluxed for 2 h. After cooling, 30 mL methanol were added dropwise within 20 min. At the same time the temperature was maintained at 10° C. to 20° C. with an ice bath. The reaction mixture was stirred for 30 min at RT and then within 30 min 45 mL of a 2M HCl solution were added dropwise thereto. The reaction mixture was concentrated by rotary evaporation i. vac. with gentle heating. The residue was diluted to approx. 200 mL with water and extracted with 200 mL EtOAc. The aqueous phase was made alkaline with a 15% (w/v) aqueous potassium carbonate solution and continuously extracted with diethyl ether overnight using a rotary perforator according to Ludwig (Messrs Normag). The organic extract was concentrated to dryness by rotary evaporation. 9.98 g of the desired product was obtained.

1. temperatureThe reaction mixture was refluxed for 2 h
2. temperatureAfter cooling
3. temperatureAt the same time the temperature was maintained at 10° C. to 20° C. with an ice bath
4. concentrationThe reaction mixture was concentrated by rotary evaporation i
5. additionThe residue was diluted to approx. 200 mL with water
6. extractionextracted with 200 mL EtOAc
7. extractioncontinuously extracted with diethyl ether overnight
8. extractionThe organic extract
9. concentrationwas concentrated to dryness by rotary evaporation