Water → HCID 10703784, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-glycidyl 4-toluenesulphonate (10.0 g), 5-chloro-2-hydroxybenzaldehyde (8.92 g) and potassium carbonate (7.87 g) in dimethylformamide (200 ml) was stirred and heated at 60° C. for 5 hours then allowed to stand for 18 hours. Water (200 ml) was added and the resultant mixture extracted with ether (3×150 ml). The combined ether extracts were washed with brine (3×150 ml), dried over magnesium sulphate and the solvent evaporated. The oily residue was purified by flash chromatography on silica eluting with a 25:1 followed by a 10:1 mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate to give (R)-5-chloro-2-(2,3-epoxypropoxy)benzaldehyde (8.1 g) contaminated with ~10% of an unknown impurity, which was used without further purification.

Provenance & Evidence