反应详情

温度

100 °C

A 28 mL Pyrex Plus tube was charged with ketone 35 (420 mg, 0.89 mmol), DMFDMA (530 mg, 4.45 mmol) and toluene (10 mL). The reaction was heated to 100° C. for 7 hours, after which more DMFDMA (530 mg, 4.45 mmol) was added, and the reaction was allowed to heat at 100° C. for 12 more hours. The reaction was then concentrated under reduced pressure, and then dissolved in 1-propanol (20 mL). The reaction was then charged with guanidine-HCl (128 mg, 1.34 mmol) and sodium methoxide (305 □L of a 25% (w/w) solution in methanol, 1.34 mmol), and the reaction was heated to 80° C. for 18 hours. The reaction was then concentrated under reduced pressure, then dissolved in 10 mL CH2Cl2, 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% heptane and ended at 100% ethyl acetate. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 37: 190 mg (41% over both steps). 1H NMR (400 MHz, CDCl3) δ 1.62 (m, 2H), 1.88 (m, 2H), 2.74 (m, 1H), 2.91 (m, 2H), 4.34 (bs, 2H), 5.14 (s, 2H), 5.21 (s, 2H), 6.48 (d, J=5.2 Hz, 1H), 6.74 (d, J=7.2 Hz, 1H), 7.09 (t, J=8.8 Hz, 2H), 7.34 (m, 5H), 7.44 (bs, 1H), 7.60 (m, 2H), 8.08 (d, J=5.2 Hz, 1H), 9.40 (d, J=7.2 Hz, 1H). MS (ESI+) 523.7.

1. temperatureto heat at 100° C. for 12 more hours
2. concentrationThe reaction was then concentrated under reduced pressure
3. dissolutiondissolved in 1-propanol (20 mL)
4. temperature1.34 mmol), and the reaction was heated to 80° C. for 18 hours
5. concentrationThe reaction was then concentrated under reduced pressure
6. dissolutiondissolved in 10 mL CH2Cl2
7. custompurified on an Isco OptiX10 CombiFlash instrument
8. additionFractions containing desired product
9. concentrationconcentrated under reduced pressure