Synthesis

To a mixed so lution of Methyl5-oxo-(E,E)-8,10-dodecadienoate (15.7g, 0.07 mol) and p-toluene sulfonylhydrazine (16.3g, 0.0875 mol) in DMF - sulfolane (350ml, 1 : 1) was added p-toluenesulfonic acid (1.75g) and sodium cyanoborohydride (17.6g, 0.28mol) at room temperature, and the solution was heated at 100 ℃ for 4 hr. After cooling to room temperature, the reaction mixture was diluted with water (1000ml) and extracted with cyclohexane. The cyclohexane solution was washed with water, dried over Na2SO4 and concentrated in vacuo. Column chromatography of the oily residue over silica gel (Merck Kieselgel 60) with petroleum ether-ether (10:1) gave 4 (5.6g, 38%) as a pale yellow liquid.A solution of Methyl (E,E)-8,10-dodecadienoate (4.2g, 0.02mol) in absolute ether (40ml) was added dropwise to a slurry of lithium aluminum hydride (0.38g, 0.01mol) in absolute ether (60 ml) with stirring at room temperature. Stirring was continued for 1 hr at room temperature. After the mixture was refluxed for I hr, the reaction was quen ched with 2NH2SO4 (30ml) and the mixture was worked up by the usual procedure to give the alcohol 5, with a nearly quantitative yield, which solidified during storage in a refrigerator, (recrystallized from pe troleum ether). The purity was 97% on GLC analysis.