Hydrochloric Acid → HCID 14748265, compound

Participants

Reaction Steps

In a dry flask under N2 was placed 150 ml of HMPA (distilled over NaH) and 15.61 g (0.14 mole) of 5-hexynoic acid, the product of Example 1b, and the mixture cooled in an ice-water bath. A solution of 190 ml of n-BuLi in hexane (0.295 mole) was added dropwise into the flask with stirring. Stirring was continued for an additional 2 hr and 37 g of 2-(4-pentylphenoxymethyl)oxirane, the product of Example 7a, was added. After 2 days stirring, the resulting reaction mixture was poured into an ice water mixture and acidified with 3N HCl. The aqueous solution was extracted with Et2O three times. The organic layers were combined and then washed with aqueous 3N NH4OH. The NH4OH solution was acidified with 3N HCl and was extracted with Et2O. The ether solution was dried over MgSO4 and solvent removed to give an oil. The oil was purified by silical gel column chromatography (CHCl3 -MeOH) and then recrystallized in petroleum ether-EtOAc to give the title compound, mp 54°-57° C.

Provenance & Evidence