Triethylamine → 5-Isoxazolecarboxylic acid, 3-(4-methylphenyl)-, methyl ester

HRID 1440329Notes

Reaction equation

HRID 1440329 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.ClN1C(=O)CCC1=O.[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][CH3:21].C(N(CC)CC)C>O.N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH:21]=[C:20]([C:19]([O:23][CH3:24])=[O:22])[O:8][N:7]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11124Methyl propionateHCID 19475HCID 19475, compoundHCID 31398Chlorosuccinimide

Product 1

HCID 7765475-Isoxazolecarboxylic acid, 3-(4-methylphenyl)-, methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Added to 100 ml of chloroform were 10.0 g (74.1 mmol) of 4-methylbenzaldoxime, 9.9 g (74.4 mmol) of N-chlorosuccinimde and 0.4 ml of pyridine. After N-chlorosuccinimide was completely dissolved, the resulting solution was stirred for further 30 minutes. Under ice cooling, 9.3 g (110.7 mmol) of methyl propionate and 9.0 g (89.1 mmol) of triethylamine were added. The resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was added with water and then extracted with chloroform. The extract was treated by a method known per se in the art. Subsequent purification on a silica gel column (eluent: chloroform) gave 3-(4-methylphenyl)-5-methoxycarbonylisoxazole as crystals.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 12 hours
  2. extractionextracted with chloroform
  3. additionThe extract was treated by a method
  4. customSubsequent purification on a silica gel column (eluent: chloroform)

Sources & evidence

ORD record
ord-e69382806e814fc69b103da4b09af3a0
Source dataset
uspto-grants-1996_03
Patent number
US05498619

Reaction notes

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