HCID 20481087, compound → HCID 11321279, compound

HRID 1026166Notes

Reaction equation

HRID 1026166 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:13])[CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 20481087HCID 20481087, compoundHCID 178418299HCID 178418299, compound

Product 1

HCID 11321279HCID 11321279, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(4-fluoro-phenyl)-pent-4-en-1-ol (4.9 g) in dichloromethane (5 ml) was added pyridimium chlorochromate (7.033 g). The reaction mixture was stirred for 16 hours at room temperature. Silica gel was added and the solvent was evaporated. Column chromatography (SiO2; heptane/EtOAc 4:1) gave 1-(4-fluoro-phenyl)-pent-4-en-1-one (4.67 g, 96%) as a light yellow liquid.MS (EI): 178.0 ([M+H]+)), 123.0 (F—C6H4CO+)

Workup

  1. additionSilica gel was added
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c6af5360aae9447a8da53a5724941c0c
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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