HCID 11241422, compound → HCID 12447362, compound

HRID 2119941Notes

Reaction equation

HRID 2119941 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>C(Cl)Cl>[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

3

Reactant 1

HCID 11241422HCID 11241422, compound

Product 1

HCID 12447362HCID 12447362, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2R)-2-benzoyloxy-1,2-epoxycyclohexane (0.030 g, 0.137 mmol, 93% ee) in anhydrous CH2Cl2 (0.4 mL) was added YbCl3 (0.0038 g, 0.0137 mmol). Upon stirring at room temperature for 30 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 (S)-2-benzoyloxy cyclohexanone (0.022 g, 73% yield, 88% 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-f3a1dd6c94ff428bb5872a4455482e4e
Source dataset
uspto-grants-2004_02
Patent number
US06686483B2

Reaction notes

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