Water → HCID 18331350, compound

Participants

Reaction Steps

1.17 g (10 mmol) of N-methylmorpholine N-oxide, 10 ml of water and 30 ml of acetone are placed in a 100 ml three-necked flask. 0.4 mol of a solution containing 1% by mass of osmium tetroxide in tert-butanol is added dropwise, followed by addition of a solution of 1.4 g (7.6 mmol) of 2,3-dimethyl-8-vinyl-quinoline in 10 ml of acetone. The reaction mixture is stirred for 2 hours at room temperature. 50 ml of water are added and the resulting mixture is extracted with ethyl acetate (3×100 ml). The organic phases are combined, washed with 100 ml of 1% sodium bisulphite solution and 100 ml of 1% sodium bicarbonate solution, dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a column of silica (elution solvent: 30% ethyl acetate in cyclohexane). 1.34 g (yield: 81%) of 2,3-dimethyl-8-(1,2-dihydroxyethyl)quinoline are obtained in the form of a white solid. m.p. =120° C.

Provenance & Evidence