3-[4-(3-Fluoro-5-methoxy-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester → HCID 57894216, compound

HRID 1822302Notes

Reaction equation

HRID 1822302 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

Participants

4

Reactant 1

HCID 690763993-[4-(3-Fluoro-5-methoxy-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

Product 1

HCID 57894216HCID 57894216, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(3-fluoro-5-methoxy-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester (0.98 g, 2.96 mmol) and 10% Pd/C (0.50 g) in ethyl acetate (50 mL) is purged with N2, and then with H2. The mixture is stirred under a hydrogen balloon for three hours. The reaction is filtered through hyflo, and the solvent is removed in vacuo to afford 0.715 g (73%) of the title compound. Rf=0.53 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C19H21O4F 332, found 333 (M+1, 100%).

Workup

  1. customis purged with N2
  2. filtrationThe reaction is filtered through hyflo
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ac854d7e976743629c6a667dffe4473e
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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