Tetrahydrofuran → HCID 10364634, compound

Participants

Reaction Steps

A mixture of benzoin (26.15 g), 8-bromooctanoic acid (25.0 g), 4-dimethylaminopyridine (1.35 g), 1,3-dicyclo-hexylcarbodiimide (25.4 g) and dry tetrahydrofuran (350 ml) was stirred under nitrogen at room temperature for 20 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness in vacuo. The residue was dissolved in dichloromethane (350 ml), washed with 5% aqueous hydrochloric acid (3×175 ml), saturated sodium hydrogen carbonate solution (2×200 ml), saturated sodium chloride solution (220 ml), dried over anhydrous magnesium sulphate and evaporated to dryness in vacuo. Column chro-matography on silica gel eluted with a hexane: dichloromethane gradient gave a yellow oil. This oil was stirred in hexane to give 2-oxo-1,2- diphenyl-ethyl 8-bromooctanoate (27.1 g, 52.7%) as a pale yellow solid m.p. 60°-61° C.

Provenance & Evidence