Sodium periodate → trans-2-(2-(Benzyloxy)-2-oxoethyl)cyclopropanecarboxylic acid

HRID 2202265Notes

Reaction equation

HRID 2202265 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[OH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>CC(C)=O.O.O.[Ru](=O)=O>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][C@@H:10]1[CH2:11][C@H:9]1[C:8]([OH:2])=[O:7])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 118622745Benzyl trans-2-(2-(hydroxymethyl)cyclopropyl)acetate

Product 1

HCID 118622753trans-2-(2-(Benzyloxy)-2-oxoethyl)cyclopropanecarboxylic acidYield 98%

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Sodium metaperiodate (107 mg, 0.50 mmol) and ruthenium(IV) oxide hydrate (3.02 mg, 0.02 mmol) were added to a solution of benzyl trans-2-(2-(hydroxymethyl)cyclopropyl)acetate (44 mg, 0.20 mmol) in acetone (1 mL) and water (1 mL) at 0° C., and the mixture was stirred at 0° C. to room temperature for 1 hr. The reaction mixture was filtered through Celite (while washing with acetone), and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give trans-2-(2-(benzyloxy)-2-oxoethyl)cyclopropanecarboxylic acid (46.0 mg, 0.196 mmol, 98%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite (while washing with acetone)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e9a9870551a641a687941ed2192f1526
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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