反应详情

温度

0 °C

To a cooled solution of 83.2G (0.92 g, 2.47 mmol) in dry THF (15 mL) at 0° C. was added LAH, 1.0 M in THF (5.0 mL, 5.0 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction (gas evolution occurred). The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-50% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 83.2H as a colorless oil (0.70 g, 82%). 1H NMR (500 MHz, CDCl3) δ ppm 7.30 (1H, m), 7.05 (1H, dd, J=10.6, 1.1 Hz), 6.97 (1H, t, J=8.9 Hz), 6.83 (2H, m), 5.52 (1H, td, J=2.4, 0.9 Hz), 4.81 (2H, s), 3.76 (3H, s), 2.25 (2H, td, J=7.1, 2.4 Hz), 1.76 (1H, br. s.), 1.69 (2H, m), 0.85 (6H, s).

1. additionUpon complete addition
2. customto quench
3. customthe reaction (gas evolution occurred)
4. extractionThe resulting solution was extracted three times with EtOAc
5. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
6. customthe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-50% EtOAc in hexanes)
7. additionFractions containing the desired product
8. concentrationconcentrated
9. customto provide 83.2H as a colorless oil (0.70 g, 82%)