反应详情

温度

0 °C

Charge a flask with trifluoro-methanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (10.0 g, 19.0 mmol) and dissolve in methylene chloride (100 mL). Add 2M HCl in ether (19 mL, 38 mmol) and remove solvent in vacuo. Redissolve in dry methylene chloride (200 mL) and cool to 0° C. under nitrogen. Add BBr3 (9.0 mL, 95 mmol) slowly, and stir at 0° C. for 30 minutes. Pour reaction slowly into saturated aqueous sodium bicarbonate and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate in vacuo. Dissolve crude material in methylene chloride (200 mL) and add N,N-diisopropylethylamine (16.5 mL, 95 mmol) and 4-dimethylaminopyridine (120 mg, 1.9 mmol) and stir at room temperature. Add acetic anhydride (3.6 mL, 38 mmol). Stir for 20 minutes and pour into saturated aqueous sodium bicarbonate. Extract with methylene chloride. Wash the organic layer with water, dry over sodium sulfate, filter and concentrate in vacuo to yield 10.5 g (100%) of acetic acid 5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-6-trifluoromethanesulfonyloxy-naphthalen-2-yl ester.

1. customremove solvent in vacuo
2. dissolutionRedissolve in dry methylene chloride (200 mL)
3. additionPour
4. extractionextract with methylene chloride
5. dry with materialDry over sodium sulfate
6. filtrationfilter
7. concentrationconcentrate in vacuo
8. dissolutionDissolve crude material in methylene chloride (200 mL)
9. stirringStir for 20 minutes
10. extractionExtract with methylene chloride
11. washWash the organic layer with water
12. dry with materialdry over sodium sulfate
13. filtrationfilter
14. concentrationconcentrate in vacuo