Oxygen → 6-Heptyn-1-ol

Participants

Reaction Steps

HO(CH2)5C≡CH was prepared by the KAPA-promoted isomerization of HOCH2C≡C(CH2)3CH3 prepared according to Millar, J. G.; Oehlschlager, A. C. J. Org. Chem. 1984, 49, 2332-2338 or HO(CH2)2C≡C(CH2)2CH3 (commercially available from GFS Chemicals; Powell, Ohio). Oxidative coupling of HO(CH2)5C≡CH was carried out in a glass reaction vessel by dissolving 6.95 grams HO(CH2)5C≡CH in pyridine/methanol (2.0 mL/6.2 mL) and adding 307 grams of CuCl followed by stirring in the presence of oxygen until all the starting material was consumed. The reaction mixture was worked up with diethyl ether and 4N HCl, the combined organic layers were dried over MgSO4, filtered and concentrated. Recrystallization of the residue from 1/1 hexanes/tert-butyl methyl ether yielded 5.35 grams of HO(CH2)5C≡C—C≡C(CH2)5OH.

Provenance & Evidence