反应详情

温度

50 °C

To a cooled (0° C.) mixture of TMEDA (11.4 mL, 76 mmol) and THF (75 mL) was added furan (5.7 mL, 78 mmol) followed by n-BuLi (15 mL, 2.5M in hexanes). The resulting solution was stirred for 30 min then ZnCl2 added (60 mL, 0.5M in THF). To this solution was added a solution comprised of (4-bromo-phenyl)-2,2-dimethyl-acetonitrile (4.48 g, 20 mmol) (reference example 30a) and (Ph3P)4Pd (460 mg, 0.4 mmol) in THF (10 mL). The resulting mixture was warmed to 50° C. and stirred at this temperature for 2.5 hr. The reaction mixture was allowed to cool to room temperature, diluted with ether, then washed, sequentially, with aqueous hydrochloric acid (2M) and brine, then dried over MgSO4 and concentrated. The residue was purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give 3.9 g of the title compound as an oil. 1H NMR (CDCl3) d 1.74 (s, 6H), 6.47 (dd, J=2, 1 Hz, 1H), 6.66 (d, J=2 Hz, 1H), 7.47 (m, 3H), 7.68 (m, 2H), MS (EI) m/z 211 (M)+.

1. temperatureTo a cooled
2. additionTo this solution was added a solution
3. stirringstirred at this temperature for 2.5 hr
4. temperatureto cool to room temperature
5. washwashed
6. dry with materialsequentially, with aqueous hydrochloric acid (2M) and brine, then dried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography (eluting with 10% ethyl acetate in hexanes)