反应详情

温度

50 °C

Dissolve 5-{[4-(2-azepan-1-yl-ethoxy)-phenyl]-hydroxymethyl}-6-(2,5-difluorophenyl)-naphthalen-2-ol (770 mg, 1.54 mmol) in 20 mL dry DMF and add sodium t-butoxide (1.18 g, 12.32 mmol). Heat the mixture to 50° C. for two hours. Dilute with water and extract multiple times with methylene chloride. Dry the organic layer and purify on a silica gel column eluting with a 0-10% methanol/methylene chloride gradient. The yield is 370 mg (50%): 1H-NMR (CDCl3, 300 MHz) δ7.76 (dd, J=12.6, 8.4 Hz, 2H); 7.58 (d, J=9.0 Hz, 1H); 7.43-7.40 (m, 1H); 7.15 (d, J=2.4 Hz, 1H); 7.05-7.01 (m, 3H); 6.89 (s, 1H); 6.83-6.80 (m, 2H); 6.66-6.63 (m, 2H); 4.00-3.98 (m, 2H); 2.92-2.92 (m, 2H); 2.78-2.78 (m, 4H); 1.66-1.59 (m, 8H). The racemic compound is purified using chiral chromatography (conditions P). The two isomers eluted with retention times of 9.9 and 13.5 minutes.

1. extractionextract multiple times with methylene chloride
2. customDry the organic layer
3. custompurify on a silica gel column
4. washeluting with a 0-10% methanol/methylene chloride gradient
5. customThe racemic compound is purified
6. washThe two isomers eluted with retention times of 9.9 and 13.5 minutes