Z-4-(2-Fluoro-3-methoxyphenyl)-4-methylpent-2-enoic acid methyl ester → 4-(2-Fluoro-3-methoxyphenyl)-4-methylpentanoic acid methyl ester

HRID 1869332Notes

Reaction equation

HRID 1869332 reaction equation
[CH3:1][O:2][C:3](=[O:18])/[CH:4]=[CH:5]\[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[F:17])([CH3:8])[CH3:7]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[F:17])([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 86599916Z-4-(2-Fluoro-3-methoxyphenyl)-4-methylpent-2-enoic acid methyl ester

Product 1

HCID 179893004-(2-Fluoro-3-methoxyphenyl)-4-methylpentanoic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

23.30 g (84.33 mmol) of E/Z-4-(2-fluoro-3-methoxyphenyl)-4-methylpent-2-enoic acid methyl ester is mixed in 310 ml of ethanol with 1.2 g of palladium on carbon, and it is stirred under hydrogen atmosphere overnight at room temperature. The catalyst is removed by filtration through a glass-fiber filter, and the residue that remains after concentration by evaporation is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 19.58 g (83.4%) of the desired compound is isolated.

Workup

  1. customThe catalyst is removed by filtration through a glass-fiber
  2. filtrationfilter
  3. concentrationafter concentration
  4. customby evaporation
  5. customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8d34c49ec49b4106b05070f7bc682225
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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