反应详情

温度

90 °C

A mixture of tert-butyl 2-(3-cyano-4-fluorophenyl)acetate (1.32 g, 5.59 mmol), N-(4-chlorophenethyl)-4-hydroxybenzamide (1.85 g, 671 mmol), and potassium carbonate (0.93 g, 6.70 mmol) in DMSO (10 ml) was stirred at 90° C. for 1 day. The reaction was cooled, diluted with ethyl acetate, and washed with 10% aqueous Na2CO3. The aqueous layer was back extracted with ethyl acetate. The organic washes were combined, washed with 10% Na2CO3 and brine, dried over sodium sulfate and concentrated. The crude material was purified by silica gel chromatography, eluting with a gradient of 5% ethyl acetate/hexanes to 60% ethyl acetate/hexanes gave tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)acetate (1.09 g, 40%).

1. temperatureThe reaction was cooled
2. washwashed with 10% aqueous Na2CO3
3. extractionThe aqueous layer was back extracted with ethyl acetate
4. washwashed with 10% Na2CO3 and brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe crude material was purified by silica gel chromatography
8. washeluting with a gradient of 5% ethyl acetate/hexanes to 60% ethyl acetate/hexanes