Potassium Carbonate → 2-[2-Fluoro-4-(2-methyl-3-oxopentyl)-phenyl]propionic acid

HRID 1506875Notes

Reaction equation

HRID 1506875 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[C:5]([F:15])[CH:4]=1.[CH3:16][CH:17]([C:23](=[O:26])[CH2:24][CH3:25])C(OCC)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:15][C:5]1[CH:4]=[C:3]([CH2:2][CH:17]([CH3:16])[C:23](=[O:26])[CH2:24][CH3:25])[CH:8]=[CH:7][C:6]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 231471Pentanoic acid, 2-methyl-3-oxo-, ethyl esterHCID 49837497Methyl 2-[4-(bromomethyl)-2-fluorophenyl]-propionate

Product 1

HCID 601554432-[2-Fluoro-4-(2-methyl-3-oxopentyl)-phenyl]propionic acidYield 70.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of compound (20) (0.78 g, 2.82 mmol), ethyl 2-methyl-3-oxopentanoate (0.46 mL, 2.82 mmol) and anhydrous potassium carbonate (0.70 g, 5.1 mmol) in acetone (40 mL) was allowed to react in the same manner as in Example 15. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (7:2) solution followed by conventional decarboxylation and hydrolysis to give 0.53 g (53%) of compound (24) of interest as clear colorless oil.

Workup

  1. customto react in the same manner as in Example 15
  2. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (7:2) solution
  3. customfollowed by conventional decarboxylation and hydrolysis

Sources & evidence

ORD record
ord-2f5bba668b0640199afea877be5176bd
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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