Pyridine → 3-Acetoxycyclohexene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-cyclohexen-1-ol (16) (45.5 mmol, 5.02 mL) in pyridine (0.27 mol, 22 mL) at 0° C., acetic anhydride was added dropwise and the reaction mixture was stirred at 0° C. for ½ h. The ice bath was removed, and the mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc, washed with HCl (1N), saturated NaHCO3, brine, and concentrated in vacuo to give 6 g (94%) of the crude product 17 which was used in the next step without further purification. TLC with 20% EtOAc/Hexane, stained with 5% H2SO4/EtOH, Rf for (16): 0.4, Rf for (17): 0.8.

Provenance & Evidence