p-Toluenesulfonic acid → HCID 9794426, compound

HRID 2119940Notes

Reaction equation

HRID 2119940 reaction equation
[C:1]([O:9][C@@:10]12[O:16][C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>[N+](C)([O-])=O>[C:1]([O:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11241422HCID 11241422, compound

Product 1

HCID 9794426HCID 9794426, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a solution of (1R, 2R)-2-benzoyloxy-1,2-epoxycyclohexane (0.030 g, 0.137 mmol, 93% ee) in anhydrous nitromethane (0.4 mL) was added p-TsOH (0.0024 g, 0.0137 mmol). Upon stirring at room temperature for 10 min, the reaction mixture was quenched with saturated NaHCO3 solution, extracted with ether, dried over anhydrous Na2SO4, filtered, concentrated, and purified on buffered silica gel (0.5-1% Et3N) by flash column chromatography [EtOAc—CH2Cl2-hexane (3:7:40)] to afford (R)-2-benzoyloxy cyclohexanone (0.0267 g, 89% yield, 90% ee).

Workup

  1. customthe reaction mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with ether
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on buffered silica gel (0.5-1% Et3N) by flash column chromatography [EtOAc—CH2Cl2-hexane (3:7:40)]

Sources & evidence

ORD record
ord-782c291e0ab24a47ae1a90814a9ee1f9
Source dataset
uspto-grants-2004_02
Patent number
US06686483B2

Reaction notes

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