HCID 20481087, compound → HCID 11321279, compound

HRID 885219Notes

Reaction equation

HRID 885219 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-25abec127cc848f49183ddf5056892d2
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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