Sodium Carbonate → 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al

Participants

Reaction Steps

4(S)-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene (4.75 g) (see Preparation 95) was dissolved in a mixture of acetonitrile (75 ml), water (13 ml) and 1N aqueous hydrochloric acid solution (17 ml). Osmium tetroxide (3.4 ml of a 0.05M solution in toluene) was added and the mixture stirred for 20 minutes. Sodium periodate (5.3 g) was then added together with a further quantity of acetonitrile (30 ml) and stirring continued overnight. Water (ca. 100 ml) was added and the acetonitrile removed under reduced pressure to give an aqueous suspension which was basified to pH>7 by the addition of solid sodium carbonate. The mixture was then extracted (three times) with ethyl acetate and the combined organic extracts washed sequentially with water and brine before being dried over anhydrous sodium sulphate. Removal of the solvent under reduced pressure gave 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al (4.3 g) as an oil.

Provenance & Evidence