Sodium Carbonate → 5-(2-Acetylfuran-3-yl)indan-1-one O-methyloxime

Participants

Reaction Steps

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]+.

Provenance & Evidence