Iodoethane → HCID 14789683, compound

Participants

Reaction Steps

Commercially available 1,5-pentanediol was mono-ethylated (2, 71%) using an equivalent of iodoethane and NaH in THF. The diol was also converted into its mono-tetrahydropyranyl ether (4, 54%) by treatment with dihydropyran and toluenesulfonic acid in methylene chloride [Ngooi et al., J. Org. Chem. 54, 911 (1989 )]. Ethoxyalcohol 2 was tosylated (pyridine, TsCl, 0° C.) in 40% yield to afford oily 3. The low yield reflects the need to distill this reactive ether. Tosylate 3 was then allowed to react with mono-THP alcohol 4 (NaH, THF, reflux, 24h) to afford, after deprotection, [Corey et al., J. Am. Chem. Soc. 91, 4318 (1969), the diether alcohol, 6, in 37% yield. Oxidation using Kiliani reagent (Na2Cr2O7 --2H2O/H2SO4 /H2O) [Kiliani and Merk, Chem. Ber. 34 3562 (1901)] afforded 6,12-dioxatetradecanoic acid, 1, in 52% yield as a colorless oil.

Provenance & Evidence