Ethyl 3-(4-fluorophenyl)-3-(4-hydroxyphenyl)-acrylate → 3-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-propionic acid ethyl ester

HRID 1160311Notes

Reaction equation

HRID 1160311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH3:14]

Participants

5

Reactant 1

HCID 68674988Ethyl 3-(4-fluorophenyl)-3-(4-hydroxyphenyl)-acrylate

Product 1

HCID 578357253-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-propionic acid ethyl esterYield 90.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 45.1 (385 mg) in ethanol (12 mL) and ethyl acetate (10 mL) was stirred with 10% Pd—C (50 mg) under a hydrogen atmosphere at room temperature for 3 h. The reaction mixture was filtered and concentrated to provide 45.2 (350 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-531869a916b64d0a9e4e2ddc7154e0c2
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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