反应详情

Compound 2 (0.80 g, 2.8 mmol) was dissolved in CH2Cl2. SOCl2 (0.61 mL, 8.3 mmol) was added dropwise. After 90 minutes, the solution was concentrated to give a yellow solid. After pumping on high vacuum for 5 minutes, the solid was dissolved in CHCl3. Et3N (2.7 mL, 19.5 mmol) was added dropwise and the reaction mixture stirred for 1 hour. The reaction was quenched with water and diluted with AcOEt. The solution was washed with sat. NH4Cl, sat. NaHCO3, brine, and then dried (MgSO4). Flash chromatography (20% AcOEt/hexane) gave both the syn (0.10 g, 14%) and anti (0.62 g, 82%) isomers 3. Anti isomer 1H NMR (400 MHz, CDCl3) δ 1.23 (t, J=7.0 Hz, 3H), 1.80 (d, J=6.6 Hz, 3H), 4.10-4.20 (m, 2H), 4.25-4.35 (m, 1H), 4.38 (brs, 1H), 5.10 (d, J=9.8 Hz, 1H), 7.17-7.25 (m, 5H), 7.59 (s, 1H). Syn isomer 1H NMR (400 MHz, CDCl3) δ 1.28 (d, J=7.0 Hz, 3H), 7.38 (t, J=7.4 Hz, 3H), 4.25-4.35 (m, 2H), 7.43-7.52 (m, 1H), 5.17 (brs, 1H), 5.23 (d, J=9.8 Hz, 1H), 7.37-7.45 (m, 5H).

1. concentrationthe solution was concentrated
2. customto give a yellow solid
3. waitAfter pumping on high vacuum for 5 minutes
4. customThe reaction was quenched with water
5. additiondiluted with AcOEt
6. washThe solution was washed with sat. NH4Cl, sat. NaHCO3, brine
7. dry with materialdried (MgSO4)
8. customFlash chromatography (20% AcOEt/hexane) gave both the syn (0.10 g, 14%) and anti (0.62 g, 82%)