反应详情

To a solution of ethylmagnesium chloride (2M in tetrahydrofuran, 10.63 mL, 21.26 mmol) under nitrogen at room temperature was added zinc chloride (0.5M in tetrahydrofuran, 5.67 mL, 2.84 mmol) via syringe. The mixture was stirred at room temperature for 1 h. The reaction mixture was brought to 0° C. and benzofuran-5-yl(phenyl)methanone (3.15 g, 14.17 mmol) in tetrahydrofuran (10 mL) was added via syringe. The reaction mixture was stirred at 0° C. for 2.5 h. The reaction mixture was cooled to room temperature and quenched with saturated aqueous NH4Cl. EtOAc was added, and the aqueous layer was separated and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to give a crude oil. The crude product was purified by silica flash chromatography (0-100% DCM/hexanes) to give 1-(benzofuran-5-yl)-1-phenylpropan-1-ol as an off-white oil. 1H NMR (400 MHz, Chloroform-d) δ ppm 7.69 (1H, d, J=1.6 Hz), 7.60 (1H, d, J=2.2 Hz), 7.39-7.45 (3H, m), 7.28-7.34 (3H, m), 7.22 (1H, tt, J=7.2, 1.4 Hz), 6.73 (1H, dd, J=2.2, 1.0 Hz), 2.38 (2H, q, J=7.3 Hz), 2.09 (1H, s), 0.90 (3H, t, J=7.3 Hz).

1. customwas brought to 0° C.
2. stirringThe reaction mixture was stirred at 0° C. for 2.5 h
3. temperatureThe reaction mixture was cooled to room temperature
4. customquenched with saturated aqueous NH4Cl
5. additionEtOAc was added
6. customthe aqueous layer was separated
7. extractionextracted with EtOAc (2×)
8. washThe combined organic layers were washed with brine
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. customto give a crude oil
12. customThe crude product was purified by silica flash chromatography (0-100% DCM/hexanes)