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

HRID 2228025Notes

Reaction equation

HRID 2228025 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 mmol), 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-03b954add18446669f315c1b698b4427
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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