反应详情

A mixture of 1-(3-bromofuran-2-yl)ethanone (A. Tanaka et al., J. Heterocycl. Chem., 1995, 32, 4 1289) (2.5 g, 13.2 mmol), the product of Example 5 Step 6 (2.83 g, 13.9 mmol), sodium carbonate (2.8 g, 27.7 mmol) in toluene (40 ml) and water (14 ml) was treated with triphenylphosphine (0.35 g, 1.3 mmol) and palladium acetate (150 mg, 0.66 mmol) and heated under reflux for 18 hours. After cooling to room temperature, the mixture was filtered through celite and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and saturated brine, dried (MgSO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with a mixture of diethyl ether/dichloromethane (5:95) to afford the title compound (2.5 g, 70%); MS(ES+) m/e 270 [M+H]+.

1. temperatureheated
2. temperatureunder reflux for 18 hours
3. filtrationthe mixture was filtered through celite
4. additionthe filtrate diluted with water and ethyl acetate
5. customThe organic phase was separated
6. washwashed with water and saturated brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customthe residue chromatographed on silica gel eluting with a mixture of diethyl ether/dichloromethane (5:95)