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

HRID 1450650Notes

Reaction equation

HRID 1450650 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-a2d91ddfa53645b79e61e6843b16eb7e
Source dataset
uspto-grants-1997_02
Patent number
US05602160

Reaction notes

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