Ethyl 3-(3-fluoro-4-methoxyphenyl)-2-methylprop-2-enoate → 3-(3-Fluoro-4-methoxy-phenyl)-2-methyl-propionic acid ethyl ester

HRID 62879Notes

Reaction equation

HRID 62879 reaction equation
[CH2:1]([O:3][C:4](=[O:17])/[C:5](/[CH3:16])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 75431686Ethyl 3-(3-fluoro-4-methoxyphenyl)-2-methylprop-2-enoate

Product 1

HCID 901182263-(3-Fluoro-4-methoxy-phenyl)-2-methyl-propionic acid ethyl esterYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

After (E)-3-(3-fluoro-4-methoxy-phenyl)-2-methyl-acrylic acid ethyl ester (0.728 g, 3.0 mmol) obtained in Step A was dissolved in EtOH (10 mL), 10% Pd/C (0.073 g) was added thereto, and the mixture was stirred at room temperature under hydrogen atmosphere for 12 hours. After the termination of the reaction, the reactant was filtered by using celite, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/2) to obtain the title compound (0.726 g, 98%).

Workup

  1. customAfter the termination of the reaction
  2. filtrationthe reactant was filtered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (eluent, EtOAc/Hex=1/2)

Sources & evidence

ORD record
ord-58a791eb5d6240f4aafbcc479548b939
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

Loading…