反应详情

A solution of NaOH (128.2 g, 3.2 mol) in 700 mL water was added to a solution of cis-2-(4-bromo-benzoyl)-cyclopentanecarboxylic acid methyl ester (166.3 g, 534.3 mmol) in MeOH (700 mL). The reaction mixture was stirred at rt overnight. NMR analysis showed that little starting material remained. After ca. 1 L solvent was removed by rotary evaporation, the mixture was diluted with 1 L water. Conc. HCl was slowly added with stirring at <15° C., to adjust the acidity to pH<6. A precipitate formed, and stirring was continued for 1 h. The solid precipitate was filtered, and rinsed with water. The dried filter cake was dissolved in 1 L EtOAc, and dried over Na2SO4. Removal of solvent and drying in vacuo afforded the desired product (131 g, 83%). 1H NMR (CDCl3) δ 7.83 (d, 2H), 7.60 (d, 2H), 4.05 (m, 1H), 3.50 (m, 1H), 2.20 (m, 2H), 2.00 (m, 1H), 1.78 (m, 3H).

1. customAfter ca. 1 L solvent was removed by rotary evaporation
2. additionthe mixture was diluted with 1 L water
3. additionConc. HCl was slowly added
4. stirringwith stirring at <15° C.
5. customA precipitate formed
6. stirringstirring
7. waitwas continued for 1 h
8. filtrationThe solid precipitate was filtered
9. washrinsed with water
10. filtrationThe dried filter cake
11. dissolutionwas dissolved in 1 L EtOAc
12. dry with materialdried over Na2SO4
13. customRemoval of solvent
14. customdrying in vacuo