Methyl 4-[2-(4-fluorophenyl)ethenyl]-3-methoxycarbonylbenzoate → Methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate

HRID 1251867Notes

Reaction equation

HRID 1251867 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 53896095Methyl 4-[2-(4-fluorophenyl)ethenyl]-3-methoxycarbonylbenzoate

Product 1

HCID 18474597Methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoateYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[2-(4-fluorophenyl)ethenyl]-3-methoxycarbonylbenzoate (56.75 g, 180.6 mrol), ethyl acetate (900 ml), 10% palladium on carbon (6 g) was stirred under an hydrogen atmosphere for 6 hours. The catalyst was filtered and replaced with fresh catalyst (6 g). The reaction was then stirred under an hydrogen atmosphere for 16 hours. The catalyst was filtered and the filtrate evaporated to dryness to give, as a colourless gum, methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate (55.00 g).

Workup

  1. filtrationThe catalyst was filtered
  2. stirringThe reaction was then stirred under an hydrogen atmosphere for 16 hours
  3. filtrationThe catalyst was filtered
  4. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-fe19f2ecf6634782a6f75f6b49ca3daf
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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