Potassium Carbonate → HCID 54448347, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-benzyloxy-3-hydroxybenzaldehyde (60.0 g), (R)-glycidyl 4-toluenesulphonate (60.0 g) and potassium carbonate (74 g) in dry dimethylformamide (600 ml) was stirred and heated at 60° C. for 14 hours. After cooling the solvent was removed in vacuo , water (250 ml) added, and the mixture extracted with ether (2×200 ml), then ethyl acetate (2×400 ml). The combined extracts were washed with brine (2×500 ml) and dried over magnesium sulphate. The solvent was removed in vacuo and the residue purified by flash chromatography on silica, pre-adsorbing onto silica first by evaporation from a solution in dichloromethane, then eluting with a 3:1 mixture of petroleum ether (b.p. 40-60° C.) and ether. Appropriate fractions were combined and the solvent removed in vacuo to give (R)-2-benzyloxy-3-(2,3-epoxypropoxy)benzaldehyde (14.22 g). A further crop of product (33.37 g) was obtained by extraction of the silica employed in the chromatography with ether (6×500 ml), followed by concentration of the combined extracts to a volume of -500 ml and cooling overnight, filtering, then washing the precipitate with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and ether. The solvent was removed from the filtrate in vacuo and the residue purified by flash chromatography by the method described above, giving a third crop (9.68 g) of product. Combined yield of product 57.27 g.

Provenance & Evidence