Trimethylsilyl iodide → 5-Benzofuranol, 2-phenyl-

Participants

Reaction Conditions

Reaction Steps

A solution of 2-phenyl-5-methoxybenzo[b]furan (K K Thomas and M M Bokadia, J Indian Chem. Soc. 1966, 43, 713) (0.5 g, 2.23 mmol) in absolute chloroform (4 ml) was treated with trimethylsilyl iodide (0.44 ml, 3.09 mmol) and warmed at 50° C. for 48 h. A further quantity (0.22 ml) of trimethylsilyl iodide was added during this period. The reaction mixture was diluted with methanol (20 ml), treated with brine (40 ml) and extracted into diethyl ether (2×40 ml). The combined extracts were washed with aqueous sodium metabisulphite, followed by brine (40 ml) and dried over sodium sulphate. After concentration in vacuo the residue was distilled to give the title compound as a colourless solid (0.41 g, 88%) b.p. 250° C., 0.1 mm Hg (Kugelrohr).

Provenance & Evidence