p-Toluenesulfonic acid → HCID 9794426, compound

HRID 1934860Notes

Reaction equation

HRID 1934860 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-fd4512d4b56d46f38a0cf2a1fb34baf6
Source dataset
uspto-grants-2002_05
Patent number
US06384265B1

Reaction notes

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