反应详情

温度

0 °C

Under a nitrogen atmosphere, add 4-hydroxybenzonitrile (4 g, 33.5 mmol), cycloheptanol (2.55 g, 22.3 mmol), tri-n-butylphosphine (8.25 mL, 33.5 mmol), and azodicarboxylate dipiperidine (8.45 g, 33.5 mmol) to anhydrous THF (60 mL) at 0° C. Stir the mixture at 0° C. for 1 h and then at room temperature for 12 h. Dilute with EtOAc (50 mL) and water (50 mL). Separate the layers and extract the aqueous phase with EtOAc (4×30 mL). Wash the combined organic extracts with water (30 mL) and brine (20 mL). Dry over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g RediSep column) eluting with hexane/EtOAc (1:0 to 1:1 gradient over 1.25 h; 80 mL/min) to provide the desired intermediate as a colorless oil (2.77 g, 58%). MS (APCI) m/z: 216 (M+H)+.

1. waitat room temperature for 12 h
2. customSeparate the layers
3. extractionextract the aqueous phase with EtOAc (4×30 mL)
4. washWash the combined organic extracts with water (30 mL) and brine (20 mL)
5. dry with materialDry over Na2SO4
6. filtrationfilter
7. concentrationconcentrate in vacuo
8. customPurify the crude mixture by chromatography on silica gel (120 g RediSep column)
9. washeluting with hexane/EtOAc (1:0 to 1:1 gradient over 1.25 h; 80 mL/min)