Trifluoromethanesulfonic anhydride → Methyl alpha-Cyclopentyl-1-Cyclohexen-1-Acetate

HRID 704697Notes

Reaction equation

HRID 704697 reaction equation
[CH:1]1([CH:6]([C:11]2(O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:1]1([CH:6]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 15158222Methyl alpha-Cyclopentyl-1-Hydroxycyclohexaneacetate

Product 1

HCID 15158223Methyl alpha-Cyclopentyl-1-Cyclohexen-1-AcetateYield 105.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The product of Example R (16.25 g, 0.068 mole) was dissolved in pyridine (100 mls) containing 3 g of 4-dimethylaminopyridine at 25° C. Trifluoromethane sulfonic anhydride (20.0 g, 0.068 moles) was added dropwise under N2 over 10 minutes. The temperature was increased to +50° C. for 15 minutes. After cooling the mixture to room temperature and stirring for 15 minutes, the reaction mixture was poured into 600 mls of 2N HCL and extracted with 1:1 ethyl acetate/ether. The organic phase was washed with brine and dried over Na2SO4. The filtration of the drying agent and removal of solvent gave 16 g of the title compound (99% yield).

Workup

  1. temperatureThe temperature was increased to +50° C. for 15 minutes
  2. additionthe reaction mixture was poured into 600 mls of 2N HCL
  3. extractionextracted with 1:1 ethyl acetate/ether
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe filtration of the drying agent and removal of solvent

Sources & evidence

ORD record
ord-771ce83162e948f7a930716299fce239
Source dataset
uspto-grants-1991_01
Patent number
US04988707

Reaction notes

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