Cornforth reagent → (E)-2-tridecen-4,7-diyn-1-al

Participants

Reaction Steps

Pyridinium dichromate (60 g) was stirred with dichloromethane (250 mL) at 0° and treated over a period of 5 min with a solution of (E)-2-tridecen-4,7-diyn-1-ol (20 g) dissolved in dichloromethane. The cooling bath was then removed and the reaction mixture was stirred for a further 3 hours (slight exotherm; maximum temperature 33°-35°). Ether (250 mL) was then added and the solids were filtered off (through paper) and washed with more ether. The combined filtrates were concentrated and the residue was treated with hexane and filtered through celite. The filtrate was then washed with water (5×250 mL), dried (MgSO4) and concentrated to a small volume (100 ml). This solution was purified by liquid chromatography (two columns, 4:1 parts by volume hexane-ethyl acetate) to give the pure (E)-2-tridecen-4,7-diyn-1-al (11 g).

Provenance & Evidence