反应详情

Freshly prepared aq. NaOH (10 M in H2O, 1.01 mmol) was added to a stirring, room temperature solution of 61 (0.0523 g, 0.2024 mmol) in MeOH (0.51 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (9 min): The reaction was concentrated, redissolved in H2O, and extracted with EtOAc. 10% aq. HCl was added dropwise to the aqueous layer until the pH=2. When a white solid did not precipitate as expected, EtOAc was added, and the organic layer was removed, dried with Na2SO4, filtered, and concentrated to provide pure 62. 1H (CD3OD, 400 MHz): δ 7.24-7.18 (2H, m), 7.17-7.05 (3H, m), 6.56 (1H, s), 3.17 (1H, app sex, J=7.3 Hz), 2.96 (1H, dd, J=13.6, 7.3 Hz), 2.80 (1H, dd, J=13.7, 7.8 Hz), 1.25 (3H, d, J=6.8 Hz) ppm. 13C(CD3OD, 100 MHz): δ 164.88, 153.40, 142.91, 140.97, 130.09, 129.25, 127.21, 106.11, 44.41, 34.96, 20.35 ppm. DEPT (CD3OD, 100 MHz): CH3 carbon: 20.35; CH2 carbon: 44.41; CH carbons: 130.09, 129.25, 127.21, 106.11, 34.96 ppm. HPLC: 8.849 min.

1. temperatureThe reaction was then heated
2. temperatureto reflux until the reaction
3. customwas judged complete by HPLC (9 min)
4. concentrationThe reaction was concentrated
5. dissolutionredissolved in H2O
6. extractionextracted with EtOAc
7. addition10% aq. HCl was added dropwise to the aqueous layer until the pH=2
8. customWhen a white solid did not precipitate
9. additionEtOAc was added
10. customthe organic layer was removed
11. dry with materialdried with Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customto provide pure 62
15. custom8.849 min.