Hydroxyamine hydrochloride → 4-(4-Methoxyphenyl)-1,2-oxazole

HRID 1798809Notes

Reaction equation

HRID 1798809 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:12]=O)[CH:10]=[O:11])=[CH:5][CH:4]=1.Cl.[NH2:15]O>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:12]=[N:15][O:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 38493702-(4-Methoxyphenyl)malondialdehyde

Product 1

HCID 185236724-(4-Methoxyphenyl)-1,2-oxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The (4-methoxyphenyl)malonaldehyde (2.5 g, 14 mmol) was heated under reflux with hydroxylamine hydrochlorid (1.46 g, 21 mmol) in ethanol (28 mL) for 2 hours. Ethanol was removed under vacuum and the residue was purified by column chromatography through a 115 gram biotage silica gel cartridge eluting with 20-50% EtOAc/hexanes to give pale oil, which solidified upon standing overnight.

Workup

  1. customEthanol was removed under vacuum
  2. customthe residue was purified by column chromatography through a 115 gram biotage silica gel cartridge
  3. washeluting with 20-50% EtOAc/hexanes
  4. customto give pale oil, which

Sources & evidence

ORD record
ord-851503766aa84406a68194a6b6600b83
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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