Salicylaldehyde oxime → Dimethyl 3-(2-hydroxyphenyl)-2-isoxazolin-5-ylphosphonate

HRID 1084806Notes

Reaction equation

HRID 1084806 reaction equation
[CH:1](=[N:9][OH:10])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].ClN1C(=O)CCC1=O.[CH:19]([P:21](=[O:26])([O:24][CH3:25])[O:22][CH3:23])=[CH2:20].C(N(CC)CC)C>ClCCl.N1C=CC=CC=1>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]1[CH2:20][CH:19]([P:21](=[O:26])([O:24][CH3:25])[O:22][CH3:23])[O:10][N:9]=1

Participants

7

Reactant 4

HCID 7200Salicylaldehyde oximeHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 78376Dimethyl vinylphosphonate

Product 1

HCID 135621431Dimethyl 3-(2-hydroxyphenyl)-2-isoxazolin-5-ylphosphonateYield 63.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

41.1 g (0.3 mol) of salicylaldoxime in dichloromethane are refluxed with 40.1 g (0.3 mol) of N-chlorosuccinimide and 1.5 ml of pyridine for 3 hours. Ice-water is added and the mixture is extracted, and the hydroxamoyl chloride is recrystallized from dichloromethane/petroleum ether. 25.5 g (0.15 mol) of this are reacted with 20.4 g (0.15 mol) of dimethyl vinylphosphonate and 22.9 ml (0.165 mol) of triethylamine in dichloromethane in analogy to Example 5 to give 25.8 g of oily product.

Workup

  1. extractionthe mixture is extracted
  2. customthe hydroxamoyl chloride is recrystallized from dichloromethane/petroleum ether

Sources & evidence

ORD record
ord-b693c24bbdb441658131117e1ee1a0fd
Source dataset
uspto-grants-1991_04
Patent number
US05006515

Reaction notes

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