(E)-4-(4-Fluoro-phenyl)-4-methyl-pent-2-enoic acid ethyl ester → 4-(4-Fluoro-phenyl)-4-methyl-pentanoic acid ethyl ester

HRID 1026123Notes

Reaction equation

HRID 1026123 reaction equation
[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[CH:6]/[C:7]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)([CH3:9])[CH3:8])[CH3:2]>CO.[Pt](=O)=O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]([C:10]1[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=1)([CH3:9])[CH3:8])[CH3:2]

Participants

4

Reactant 1

HCID 67177264(E)-4-(4-Fluoro-phenyl)-4-methyl-pent-2-enoic acid ethyl ester

Product 1

HCID 671771124-(4-Fluoro-phenyl)-4-methyl-pentanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-4-(4-fluoro-phenyl)-4-methyl-pent-2-enoic acid ethyl ester (4.10 g) in methanol (150 ml) at room temperature was added platinum(IV) oxide (788 mg). The mixture was stirred under an atmosphere of hydrogen (1 atm) at room temperature for 2 h. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to yield a yellow oil, (3.97 g, 96%); MS (ISP): 239.2 ([M+H]+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto yield a yellow oil, (3.97 g, 96%)

Sources & evidence

ORD record
ord-4026d0ab01924658947eebdb4f517109
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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