反应详情

温度

-78 °C

To a solution of 12c (32 mg, 0.063 mmol) in 1 mL THF at −78° C., was added LiHMDS (157 μL, 0.157 mmol). The mixture was stirred at −78° C. for 10 min, then cinnamyl bromide (18.6 mg, 0.095 mmol) in 250 μL THF was added. The reaction was stirred at −78° C. for 1.5 h, then quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with sat NH4Cl and brine, dried (Na2SO4), and concentrated. The crude mixture was purified by flash chromatography (35% EtOAc/hexanes) to afford 26.0 mg (66%) of 116a. 1H NMR (300 MHz, CDCl3) δ9.57 (br s, 1H), 7.74 (br s, 1H), 7.47 (d, J=8.1, 2H), 7.29-7.23 (m, 17H), 7.07 (t, J=7.5, 1H), 6.47 (d, J=15.7, 1H), 6.02-5.97 (m, 1H), 5.20-5.17 (m, 3H), 4.80 (br s, 1H), 2.70-2.41 (m, 4H), 1.48 (s, 3H).

1. stirringThe reaction was stirred at −78° C. for 1.5 h
2. customquenched with sat. NH4Cl
3. additionThe mixture was diluted with EtOAc
4. washwashed
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe crude mixture was purified by flash chromatography (35% EtOAc/hexanes)