Allyl Alcohol → 14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal

Participants

Reaction Steps

The allyl alcohol compound shown above [14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol] (492 mg, 1.51 mmol) obtained in Reference Example 1 was dissolved in methylene chloride (22 ml). To the solution was added powdery barium manganate (8.5 g), and the resultant mixture was stirred under argon atmosphere. Disappearance of the starting material was confirmed eight hours later, and the mixture was filtered and washed. The filtrate and washings were combined and concentrated. The residue was chromatographed on a silica gel column (Eluent:n-hexane:ethyl acetate=15:1) to give the objective 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal (468 mg, 95%).

Provenance & Evidence