Hydroxyamine hydrochloride → Methyl 4-{3-[4-(pentyloxy)phenyl]-1,2-oxazol-5-YL}benzoate

HRID 1386618Notes

Reaction equation

HRID 1386618 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:16]=2)=O)=[CH:7][CH:6]=1)=[O:4].Cl.[OH:28][NH2:29]>C(O)C.C(OCC)(=O)C.ClCCCl.[O-2].[Mn+4].[O-2]>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[CH:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[O:28][N:29]=2)=[CH:16][CH:17]=1)[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 541783721-(4-Methoxycarbonylphenyl)-3-(4-n-pentyloxyphenyl)-1-propene-3-one

Product 1

HCID 21182499Methyl 4-{3-[4-(pentyloxy)phenyl]-1,2-oxazol-5-YL}benzoateYield 23.6%

Reagents, catalysts & solvents 4

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-Methoxycarbonylphenyl)-3-(4-n-pentyloxyphenyl)-1-propen-3-one (4.0 g) and hydroxyamine hydrochloride (3.93 g) in ethanol (40 ml) was refluxed for 4 hours. The mixture was diluted with ethyl acetate, and the organic layer was washed with water (×2), brine and dried over magnesium sulfate. The solvents were removed under reduced pressure to give crude oxime. To a solution of crude oxime in 1,2-dichloroethane (20 ml) was added activated-manganese(IV) oxide (10.0 g). The reaction mixture was refluxed for 2 hours and filtered. The residue was washed with dichloromethane. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile. The solid was collected by filtration and dried to give Methyl 4-[3-(4-n-pentyloxyphenyl)isoxazol-5-yl]benzoate (0.98 g).

Workup

  1. washthe organic layer was washed with water (×2), brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvents were removed under reduced pressure
  4. customto give crude oxime
  5. temperatureThe reaction mixture was refluxed for 2 hours
  6. filtrationfiltered
  7. washThe residue was washed with dichloromethane
  8. customThe solvents were removed under reduced pressure
  9. customthe residue was triturated with acetonitrile
  10. filtrationThe solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-46ccb1d39d8547b9b724a41c8a6ec8b7
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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