3,5-Dimethyl-4-(hydroxymethyl)isoxazole → 3,5-Dimethyl-4-Isoxazolecarbaldehyde

HRID 1058362Notes

Reaction equation

HRID 1058362 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([CH3:9])[O:4][N:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[C:5]([CH3:9])[O:4][N:3]=1

Participants

4

Reactant 1

HCID 2895753,5-Dimethyl-4-(hydroxymethyl)isoxazole

Product 1

HCID 2895763,5-Dimethyl-4-IsoxazolecarbaldehydeYield 37%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Manganese dioxide (5.48 g, 62.9 mmol) and dichloromethane (20 mL) were added to a solution of 3,5-dimethylisoxazole-4-methanol (prepared according to the literature procedure: Saucy, G.; Scott, J. W. U.S. Pat. No. 3,984,428 Oct. 5, 1976; 1.00 g, 7.9 mmol) in dichloromethane (25 mL). The mixture was stirred at room temperature overnight, then filtered through Celite®, evaporated under reduced pressure and the residual material was chromatographed over silica gel (10% ethyl acetate/hexanes) to give 3,5-dimethylisoxazole-4-carboxaldehyde (365 mg, 37% yield) as a colorless solid.

Workup

  1. customprepared
  2. filtrationfiltered through Celite®
  3. customevaporated under reduced pressure
  4. customthe residual material was chromatographed over silica gel (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8b1df681e7fa4b5c9812b429ebacfa59
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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