Sulfuric acid magnesium salt (1:1) → 5-Methyl-3-phenylisoxazole-4-carboxaldehyde

HRID 1695466Notes

Reaction equation

HRID 1695466 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2].[CH3:18][C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20]=1[CH2:30][OH:31]>ClCCl.C(OCC)C>[CH3:18][C:19]1[O:23][N:22]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20]=1[CH:30]=[O:31]

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 27761445-Methyl-3-phenylisoxazole-4-carboxaldehydeYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of pyridinium chlorochromate (19.4 g, 90.0 mmol) and anhydrous magnesium sulfate (36 g) in dichloromethane (100 mL) was added a solution of (5-methyl-3-phenyl-4-isoxazolyl)methanol (14.0 g, 74.0 mmol) in dichloromethane (50 mL) and the resulting solution stirred under argon for 2 h. The solution was then dissolved in diethylether (100 mL), filtered through silica and concentrated to give a viscous brown oil. Purification by chromatography (silica, heptane:ethyl acetate 9:1 to 3:2) afforded the title compound (10.5 g, 76%) which was obtained as a white solid. MS: m/e=188.2 [M+H]+.

Workup

  1. filtrationfiltered through silica
  2. concentrationconcentrated
  3. customto give a viscous brown oil
  4. customPurification by chromatography (silica, heptane:ethyl acetate 9:1 to 3:2)

Sources & evidence

ORD record
ord-eee344c8a7dc4bb09ec368891d40ac05
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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