benzyl 4-fluorotetrahydro-2H-pyran-4-carboxylate → 4-Fluorooxane-4-carboxylic acid

HRID 2047473Notes

Reaction equation

HRID 2047473 reaction equation
[F:1][C:2]1([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1>C(O)C.C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[F:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 67232515benzyl 4-fluorotetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 401522694-Fluorooxane-4-carboxylic acidYield 78%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of the compound (0.18 g) obtained in step 2 and 20% palladium hydroxide (0.02 g) in ethanol/ethyl acetate (2/1 mL) was stirred under a hydrogen atmosphere (1 atm) at room temperature for 4 hr. The reaction mixture was filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/hexane to give the title compound (0.084 g, 78%) as a gray powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ff511a7563274246842e3606caf99736
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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