Tetrahydrofuran → HCID 18316645, compound

Participants

Reaction Steps

7-Bromo-4-methoxybenzoxazole (630 mg), triethylamine (3.85 ml), triphenylphosphine (290 mg), bis(triphenylphosphine)palladium chloride (88 mg), water (20 ml) and tetrahydrofuran (40 ml) were combined and heated to 90° C. in a Parr apparatus under 1035 kPa (150 psi) of carbon monoxide for 3 days. After cooling to room temperature, the tetrahydrofuran was evaporated. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous phase was acidified to pH4 with acetic acid, and the layers separated. The aqueous phase was extracted with ethyl acetate (2×30 ml) followed by dichloromethane (2×30 ml). The combined organic phases were dried over magnesium sulphate and evaporated in vacuo. Purification of the residue by flash chromatography eluting with ethyl acetate and trituration with diethyl ether afforded the title compound as a white solid (125 mg). On standing, a white solid precipitated in the water layer which was removed by filtration and dried in vacuo at 45° C. for 1 hour to give a further portion of the title compound as a white solid (49 mg).

Provenance & Evidence