4-(3-Fluorophenyl)-3-buten-1-ol → 3-Fluoro-benzenebutanol

HRID 363081Notes

Reaction equation

HRID 363081 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 536388864-(3-Fluorophenyl)-3-buten-1-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 540408183-Fluoro-benzenebutanolYield 89.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a reaction vessel were placed 0.53 g of 4-(3-fluorophenyl)-3-buten-1-ol and 50 ml of ethyl acetate, and the air in the vessel was exchanged for nitrogen. Then, 0.1 g of 10% palladium carbon was added thereto, and the nitrogen in the vessel was exchanged for hydrogen, followed by vigorous stirring at room temperature for 24 hours. After the hydrogen in the vessel was exchanged for nitrogen, the reaction solution was filtered through a celite bed, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.48 g of 4-(3-fluorophenyl)-1-butanol.

Workup

  1. customIn a reaction vessel were placed
  2. filtrationthe reaction solution was filtered through a celite bed
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-329321572bed4df2bf1df618f2db5072
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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