Diethyl Ether → HCID 5283269, compound

Participants

Reaction Steps

0.6 g of diethyl 6-propyl-2,5-nonadienylphosphonate was dissolved in 10 ml. of tetrahydofuran, and an equivalent amount of n-butyl lithium was added at -60° C. in an atmosphere of argon. To this solution was further added 0.56g of 4-butyl iodide-1-tetrahydropyranyl ether. The temperature of the reaction system was gradually elevated to room temperature. The reaction mixture was poured into ice water, and extracted with ether. Concentration of the solvent gave a pale yellow viscous oily substance. The oily product was dissolved in 20 ml. of ether, and reduced with 0.2 g of lithium aluminum hydride to afford 0.5g of 10-propyl-trans-5,9-tridecadiene-1-tetrahydropyranyl ether in a yield of 80%. This ether was treated with a catalytic amount of p-toluenesulfonic acid in methanol to split off the protective group. Thus, there was obtained pure 10-propyl-trans-5,9-tridecadienol in a quantitative yield. The properties of this product were as follows:

Provenance & Evidence