反应详情

温度

60 °C

A suspension of 1.75 g (5.6 mmol) 1-7 in 15 mL of EtOH and 10 mL of 3 M NaOH was heated at 60° C. for 3 h, cooled to room temperature and dumped into a separatory funnel with EtOAc and brine. The layers were separated, the aqueous phase was extracted twice with EtOAc, the combined organic phases were washed twice with brine, dried over Na2SO4, and concentrated to provide a white solid. To this flask was added 30 mL of CH2Cl2, 1.5 g (22.3 mmol) of imidazole and 1.76 g (11.7 mmol) of TBSCl, and the resultant suspension was stirred overnight. The reaction was diluted with CH2Cl2, washed twice with water, dried over Na2SO4, concentrated, and the residue purified by silica gel chromatography with EtOAc/hexanes to provide 1-8 as a white solid. Data for 1-8: 1HNMR (500 MHz, CDCl3) δ 7.6-7.3 (m, 5H), 7.1-6.9 (m, 3H), 6.75 (s, 1H), 4.25 (d, 1H), 4.1 (d, 1H), 3.95 (d, 1H), 3.75 (d, 1H), 0.9 (s, 9H), 0.1 (s, 3H), 0.05 (s, 3H) ppm.

1. temperaturecooled to room temperature
2. customThe layers were separated
3. extractionthe aqueous phase was extracted twice with EtOAc
4. washthe combined organic phases were washed twice with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customto provide a white solid
8. washwashed twice with water
9. dry with materialdried over Na2SO4
10. concentrationconcentrated
11. customthe residue purified by silica gel chromatography with EtOAc/hexanes