Ethyl Acetate → 2-(2,6-Difluorophenyl)-4-(4-formylphenyl)oxazoline

HRID 479580Notes

Reaction equation

HRID 479580 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=CC3C=CC=CC=3)=[CH:16][CH:15]=2)[N:13]=1.I([O-])(=O)(=O)=[O:29].[Na+].C(OCC)(=O)C>C(#N)C.CC(C)=O.O.O.[Ru](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[O:29])=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 695488982-(2,6-Difluorophenyl-)4-(4-(2-phenylethenyl)phenyl)oxazoline

Product 1

HCID 120566362-(2,6-Difluorophenyl)-4-(4-formylphenyl)oxazolineYield 97.5%

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 18799168Acetonitrile acetone waterSolvent

Procedure

At 0° C., 2-(2,6-difluorophenyl-)4-(4-(2-phenylethenyl)phenyl)oxazoline (7.22 g, 20 mmol) and sodium metaperiodate (8.55 g, 20 mmol) were suspended in acetonitrile/acetone/water (1:1:1, 180 ml), and a catalytic amount of ruthenium trichloride hydrate was added. Following extractive work-up with ethyl acetate and column chromatography, 5.6 g of the aldehyde were obtained as a viscous oil.

Workup

  1. customAt 0° C.

Sources & evidence

ORD record
ord-b438d3c89a524794985ad3aecba2fad6
Source dataset
uspto-grants-2003_11
Patent number
US06645984B2

Reaction notes

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