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

HRID 1742532Notes

Reaction equation

HRID 1742532 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. Analytical results of the crystals obtained: Yield: 8.0 g (49.8%). Melting point: 106°-108° C.

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-14d58ecc97044c23889974023da63f6f
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

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