反应详情

A solution of 23 (150 mg, 0.329 mmol) in 3.29 mL of a 1:2:3 solution of H2O:MeOH:THF was stirred with LiOH. H2O (69 mg, 1.65 mmol) for 1 hour when LCMS demonstrated complete conversion of starting materials to product. The reaction mixture was dried under reduced pressure and the residue was suspended in water and the pH was adjusted to 11 with aqueous 1N NaOH solution. The aqueous layer was washed with EtOAc twice. The pH of the aqueous layer was then adjusted to 5 using 1N HCl and the product was extracted with CH2Cl2 under continuous extraction conditions. The organic layer was dried in vacuo to yield the product 24 as an orange solid. 1H NMR (300 MHz, CDCl3) δ 2.1 (s, 1H), 2.25-2.45 (m, 4H), 4.04 (s, 3H), 4.43 (d, 1H, J=15 Hz), 5.32 (dd, 1H, J=3, 14 Hz), 5.49 (s, 1H), 7.03 (t, 2H, J=9 Hz), 7.35 (dd, 2H, J=5, 8 Hz), 7.57 (dd, 1H, J=4, 8 Hz), 8.52 (dd, 1H, J=2, 8 Hz), 8.98 (dd, 1H, J=2, 5 H); 13C NMR (75 MHz, CD3OD) δ 21.4, 33.6, 41.9, 61.8, 61.9, 112.3, 115.7, 116.0, 123.1, 125.0, 126.5, 130.4, 130.5, 131.8, 131.8, 139.3, 142.6, 148.3, 149.6, 162.4 (d, J=245 Hz), 167.2, 175.3; 19F NMR (282.6 MHz, CDCl3) δ 62.6; EI MS (m/z) 441.4 [M−H]−, 883.1 [2M−2H]−.

1. customThe reaction mixture was dried under reduced pressure
2. washThe aqueous layer was washed with EtOAc twice
3. extractionthe product was extracted with CH2Cl2 under continuous extraction conditions
4. customThe organic layer was dried in vacuo