Ethyl 3,3-bis(4-fluorophenyl)acrylate → Ethyl 3,3-bis(4-fluorophenyl)propanoate

HRID 2190300Notes

Reaction equation

HRID 2190300 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H][H]>[Pd].CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 21908058Ethyl 3,3-bis(4-fluorophenyl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 23522917Ethyl 3,3-bis(4-fluorophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3,3-bis(4-fluorophenyl)acrylate, prepared in the previous step, and palladium (10% weight on carbon, 2.68 g, 25.2 mmol) under a nitrogen atmosphere was added EtOH (100 mL). The nitrogen atmosphere was replaced by hydrogen from a double balloon and the reaction mixture was stirred at room temperature. After 16 h, the reaction mixture was filtered through a pad of Celite and concentrated to give ethyl 3,3-bis(4-fluorophenyl)propanoate which was used in the next step without further purification.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c754dd11be5d4d19a08c9163c9cc979f
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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