1-Butanol → HCID 15407953, compound

Participants

Reaction Steps

3.86 g (28.6 mmol) of N-methylmorpholine N-oxide, 10 ml of water and 20 ml of acetone are placed in a 100 ml three-necked flask. 2.1 ml of a 1% by mass solution of osmium tetroxide in tort-butanol are added dropwise, followed by a solution of 5.2 g (26 mol) of 2,3-dimethyl-7-ethenylbenzofuran in 10 ml of acetone. The reaction mixture is stirred for 5 hours at room temperature. 100 ml of water are added and extraction is carried out with ethyl acetate (3×150 ml). The organic phases are combined, washed with 100 ml of a 1% sodium bisulphite solution and 100 ml of a 1% sodium bicarbonate solution, dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a silica column (elution solvent: 35% ethyl acetate in cyclohexane). 4.2 g (Yield: 85%) of 2,3-dimethyl-7-(1,2-dihydroxyethyl)benzofuran are obtained in the form of a white solid. M.p.=93-95° C.

Provenance & Evidence