Ethyl 3-(4-fluoro-3,5-dimethylphenyl)-2-methylacrylate → Ethyl 2-(4-fluoro-3,5-dimethylbenzyl)propanoate

HRID 1158127Notes

Reaction equation

HRID 1158127 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:3]=1[CH3:17]>CO.[Pd]>[F:1][C:2]1[C:3]([CH3:17])=[CH:4][C:5]([CH2:9][CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 68642179Ethyl 3-(4-fluoro-3,5-dimethylphenyl)-2-methylacrylate

Product 1

HCID 59512575Ethyl 2-(4-fluoro-3,5-dimethylbenzyl)propanoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Ethyl 3-(4-fluoro-3,5-dimethylphenyl)-2-methylacrylate (0.190 g, 0.855 mmol) in 10 mL of MeOH, was added Pd (10 wt % on activated carbon, 0.038 g). After stirring at room temperature under H2 (1 atm) for 40 h, the reaction mixture was filtered through a pad of Celite and washed with MeOH. The filtrate was concentrated under reduced pressure. The crude product was used directly in the next step without further purification (0.138 g, 88% yield). LC-MS: tR=10.9 min; m/z 239 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe crude product was used directly in the next step without further purification (0.138 g, 88% yield)

Sources & evidence

ORD record
ord-7244cb3929d24fabb49ea6f9b3be2a9b
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

Loading…