反应详情

Freshly prepared aq. NaOH (10 M in H2O, 0.947 mmol) was added to a stirring, room temperature solution of 57 (0.0489 g, 0.1893 mmol) in MeOH (0.47 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (8 min): The reaction was concentrated, redissolved in H2O, and extracted with EtOAc (1 mL): 10% aq. HCl was added dropwise to the aqueous layer until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 0.0298 g (68.3%) of 58. 1H (CD3OD, 400 MHz): δ 7.24 (2H, t, J=7.3 Hz), 7.18 (2H, d, J=7.3 Hz), 7.14 (1H, t, J=7.3 Hz), 6.42 (1H, s), 3.11-3.01 (1H, m), 2.95 (1H, dd, J=14.1, 7.3 Hz), 2.89 (1H, dd, J=14.1, 7.8 Hz), 1.26 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, 100 MHz): δ 164.83, 147.35, 147.13, 143.02, 129.45, 127.92, 127.35, 108.07, 41.46, 35.58, 22.05 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 22.05; CH2 carbons: 35.58; CH carbons: 129.45, 127.92, 127.35, 108.07, 41.46 ppm. HPLC: 8.764 min.

1. temperatureThe reaction was then heated
2. temperatureto reflux until the reaction
3. customwas judged complete by HPLC (8 min)
4. concentrationThe reaction was concentrated
5. dissolutionredissolved in H2O
6. extractionextracted with EtOAc (1 mL)
7. addition10% aq. HCl was added dropwise to the aqueous layer until the pH=2
8. customThe white solid that precipitated from the reaction
9. filtrationwas filtered off
10. washwashed with cold H2O
11. customThe solid was dried under vacuum overnight