反应详情

To a cold (0° C.) solution of (buta-1,3-dien-2-yloxy)trimethylsilane (1.86 mL, 10.6 mmol) in DCM (80 mL) was 6-bromo-5-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one (Intermediate 5, 2.32 g, 9.62 mmol) added. Boron trifluoride diethyl etherate (0.594 mL, 4.81 mmol) was added at 0° C. The reaction was stirred for 30 min., and then quenched with MeOH (1.0 mL). The reaction mixture was acidified with aq. 2 M HCl solution, and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated. The product was purified by flash column chromatography using a stepwise gradient of heptane/EtOAc (7:1-3.5:1-1:1), to give the title compound (1.60 g, 53% yield). 1H NMR (500 MHz, CDCl3) δ ppm 1.83-1.94 (m, 2 H) 2.17-2.27 (m, 2 H) 2.38-2.51 (m, 2 H) 2.72 (dt, 2 H) 3.18 (s, 2 H) 7.25 (d, 1 H) 8.01 (d, 1 H); MS (ES+) m/z 311,313 [M+H]+.

1. additionadded
2. customquenched with MeOH (1.0 mL)
3. extractionextracted with DCM
4. washThe organic phase was washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe product was purified by flash column chromatography