反应详情

Perchloric acid (70%, 0.28 mL, 3.2 mmol) was added to a solution of (S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate (0.82 g, 1.6 mmol) in tert-butyl acetate (5 mL) at room temperature. After 3 h, solid NaHCO3 was added and the slurry stirred vigorously for 30 min. Saturated NaHCO3 was added slowly until the mixture was pH ˜8. Following extraction of the organic layer with EtOAc, the combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The resulting residue was purified by Yamazen column chromatography (0-35% EtOAc/Hex) to produce 0.52 g (57%) of the title compound as an amorphous solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.69 (s, 1H); 7.66 (d, J=2.4 Hz, 1H); 7.51 (m, 2H); 7.44 (m, 1H); 7.34 (d, J=9.4 Hz, 1H); 7.27 (m, 1H); 7.15 (dd, J=9.4, 2.4 Hz, 1H); 5.12 (s, 1H); 4.17 (m, 2H); 2.63 (s, 3H); 1.23 (t, J=7.2 Hz, 3H); 1.01 (s, 9H).

1. extractionextraction of the organic layer with EtOAc
2. washthe combined organics were washed with brine
3. dry with materialdried over anhydrous MgSO4
4. concentrationconcentrated in vacuo
5. customThe resulting residue was purified by Yamazen column chromatography (0-35% EtOAc/Hex)