Sodium borohydride → 5-Cyclohexadecen-1-one

Participants

Reaction Steps

A mixture of 1,2-divinylcyclododecan-1-ol (0.125 g, 5.10-4 mol) and mercuric trifluoroacetate (0.215 g) in methylene chloride (4 cc) is kept at a temperature of the order of 20° C. After a reaction time of 1 hour 30 minutes, a solution of sodium borohydride (0.005 g) in 3 N sodium hydroxide solution (0.33 cc) is added to the reaction mixture. The reaction mixture is extracted with methylene chloride (3×10 cc). The organic extracts are dried over magnesium sulphate. After filtration and concentration of the solvent under reduced pressure (20 mm Hg; 2.7 kPa), cyclohexadec-5-en-1-one (0.087 g) is obtained with a yield of 70%.

Provenance & Evidence