(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol → 5-Methyl-3-phenylisoxazole-4-carboxaldehyde

HRID 1942271Notes

Reaction equation

HRID 1942271 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14]>ClCCl.[O-2].[Mn+4].[O-2]>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH:13]=[O:14]

Participants

4

Reactant 1

HCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 27761445-Methyl-3-phenylisoxazole-4-carboxaldehydeYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-methyl-3-phenyl-4-isoxazolyl)methanol (8.0 g, 42 mmol) in dichloromethane (1 L) was added manganese(IV) oxide (81.7 g, 0.85 mol) and the resulting mixture stirred vigorously for 7 days. The mixture was then filtered and the filtrate evaporated to afford the title compound (7.1 g, 89%) as a light yellow solid. MS: m/e=188.2 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-60aa2e272f1b42e1a03f2711af632814
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

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