Triacetoxyperiodinane → Benzyl 2-keto-2-cyclopentylacetate

HRID 1774387Notes

Reaction equation

HRID 1774387 reaction equation
[CH:1]1([CH:6]([OH:17])[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[O:17]=[C:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 54305517Benzyl 2-cyclopentyl-2-hydroxyacetate

Product 1

HCID 18370535Benzyl 2-keto-2-cyclopentylacetateYield 79.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of benzyl 2-cyclopentyl-2-hydroxyacetate (1.76 g, 7.5 mmol) in dichloromethane (30 mL) was added Dess-Martin reagent (5 g, 11.8 mmol), and the mixture was stirred at room temperature for 15 h. The reaction mixture was diluted with 10% sodium thiosulfate, and extracted with diethyl ether. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, and brine, dried over anhydrous magnesium sulfate, filtered, and the organic solvent in the filtrate was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate 9:1) to give 1.383 g of the title compound as oil (yield: 79%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe organic solvent in the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9d7fb8262adb424eb87032ec96b0a237
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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