反应详情

To a stirred solution of Compound 2B (3.26 g, 5.94 mmol) in THF (100 mL) was added TFA (2.74 mL, 35.63 mmol) followed by DDQ (7.01 g, 30.88 mmol) in THF (40 mL). The reaction was stirred at room temperature over the weekend. The reaction was quenched with water (100 mL) and then poured into water (600 mL) and dichloromethane (100 mL). Solid NaHCO3 (100 g) was added and the mixture stirred for approximately 30 minutes. Dichloromethane (200 mL) was added and the mixture filtered. The collected filtrate was transferred to a separating funnel and the layers separated. The aqueous layer was extracted with dichloromethane (2×100 mL) and the combined organics washed with water (3×100 mL, brine (100 mL) and dried over MgSO4. After filtration, the volatiles were removed. The crude material was purified by silica chromatography eluting 0-4% Methanol/(1:1 ethyl acetate/dichloromethane). The oil was recrystallized from methanol to give Compound 2, (2.03 g, 3.72 mmol, 63% yield). 1H-NMR (300 MHz, CDCl3) δ 7.63 (1H, d), 7.45 (1H, d), 7.19-7.06 (2H, m), 6.99-6.90 (1H, m), 6.88-6.78 (2H, m), 6.52 (1H, d), 6.33 (2H, s), 4.06 (2H, t), 3.17-2.99 (4H, bs), 2.74-2.43 (6H, m), 2.35 (2H, t), 1.94-1.54 (6H, m), 0.93 (3H, t).

1. customThe reaction was quenched with water (100 mL)
2. additionpoured into water (600 mL) and dichloromethane (100 mL)
3. additionSolid NaHCO3 (100 g) was added
4. stirringthe mixture stirred for approximately 30 minutes
5. additionDichloromethane (200 mL) was added
6. filtrationthe mixture filtered
7. customThe collected filtrate was transferred to a separating funnel
8. customthe layers separated
9. extractionThe aqueous layer was extracted with dichloromethane (2×100 mL)
10. washthe combined organics washed with water (3×100 mL, brine (100 mL)
11. dry with materialdried over MgSO4
12. filtrationAfter filtration
13. customthe volatiles were removed
14. customThe crude material was purified by silica chromatography
15. washeluting 0-4% Methanol/(1:1 ethyl acetate/dichloromethane)
16. customThe oil was recrystallized from methanol