反应详情

Benzyl carbonate 37 (190 mg, 0.36 mmol) was slurried in CH3CN (5 mL) in a 28 mL Pyrex Plus tube. TMSI (720 mg, 3.6 mmol) was then added, and the reaction was allowed to stir at room temperature for 2 hours. The reaction was then concentrated under reduced pressure. The crude product was then dissolved in 10 mL CH2Cl2, plus a few drops of methanol, then loaded onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 38: 140 mg (100%). 1H NMR (400 MHz, CDCl3) δ 1.67 (m, 2H), 1.84 (m, 2H), 2.67 (m, 1H), 2.74 (m, 2H), 3.18 (m, 2H), 5.03 (s, 2H), 6.44 (d, J=5.2 Hz, 1H), 6.77 (d, J=7.2 Hz, 1H), 7.05 (t, J=8.8 Hz, 2H), 7.43 (bs, 1H), 7.56 (m, 2H), 8.04 (d, J=5.2 Hz, 1H), 9.36 (d, J=7.2 Hz, 1H). MS (ESI+) 389.2.

1. concentrationThe reaction was then concentrated under reduced pressure
2. dissolutionThe crude product was then dissolved in 10 mL CH2Cl2
3. custompurified on an Isco OptiX10 CombiFlash instrument
4. additionFractions containing desired product
5. concentrationconcentrated under reduced pressure