反应详情

温度

0 °C

The product from Example 106B (4.67 g, 22.3 mmol), NaI (3.343 g, 22.3 mmol), and NaOH (892 mg, 22.3 mmol) were combined in methanol (70 mL) at 0° C. and treated with bleach (5.25%, 31.6 g) dropwise over 30 minutes. After being stirred at 0° C. for 80 minutes, the mixture was quenched with 10% aqueous sodium thiosulfate (10 mL). The mixture was acidified with 1M aqueous HCl (25 mL), neutralized with dipotassium hydrogen phosphate, recooled to 0° C., and filtered. The solids were rinsed with water, then mostly dissolved in 50% EtOAc/hexanes and filtered. When this filtrate was mostly concentrated crystals began to form. The solids were slurried with 20% EtOAc/hexanes, collected by filtration, and washed with 10% EtOAc/hexanes followed by hexanes to provide the impure title compound as a light tan powder (52% yield). MS (ESI APCI negative ion detection) m/z 334 (M−H)−; 1HNMR (300 MHz, d6-DMSO) δ 2.52 (s, 3H), 6.98 (d, 1H), 7.58-7.63 (m, 2H), 7.73 (s, 1H), 7.78 (d, 1H), 8.06 (d, 1H), 10.66 (s, 1H).

1. additiontreated with bleach (5.25%, 31.6 g) dropwise over 30 minutes
2. customthe mixture was quenched with 10% aqueous sodium thiosulfate (10 mL)
3. customrecooled to 0° C.
4. filtrationfiltered
5. washThe solids were rinsed with water
6. dissolutionmostly dissolved in 50% EtOAc/hexanes
7. filtrationfiltered
8. customto form
9. filtrationcollected by filtration
10. washwashed with 10% EtOAc/hexanes