Pyridine → 3-Acetoxycyclohexene
Reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.N1C=CC=CC=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)(=[O:16])[CH3:15]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- customThe ice bath was removed
- stirringthe mixture was stirred at room temperature overnight
- additionThe mixture was diluted with EtOAc
- washwashed with HCl (1N), saturated NaHCO3, brine
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-611c55a3640e4f30b7b46d3e8e76f005
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404725B2
Reaction notes
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