Chloride → Methyl 3-tert.butyl-2-isoxazolin-5-yl(P-methyl)phosphinate

HRID 1084799Notes

Reaction equation

HRID 1084799 reaction equation
[CH:1](=[N:6][OH:7])[C:2]([CH3:5])([CH3:4])[CH3:3].ClN1C(=O)CCC1=O.[Cl-].[CH:17]([P:19]([CH3:23])(=[O:22])[O:20][CH3:21])=[CH2:18].C(N(CC)CC)C>ClCCl.N1C=CC=CC=1>[C:2]([C:1]1[CH2:18][CH:17]([P:19]([CH3:23])(=[O:22])[O:20][CH3:21])[O:7][N:6]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

8

Reactant 5

HCID 312ChlorideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 136457PivalaldoximeHCID 6454580Methyl methylvinylphosphinate

Product 1

HCID 20062412Methyl 3-tert.butyl-2-isoxazolin-5-yl(P-methyl)phosphinateYield 50%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

40.4 g (0.4 mol) of pivalaldoxime are converted in analogy to Example 1(a) with 58.7 g (0.44 mol) of N-chlorosuccinimide and 2 ml of pyridine in dichloromethane into the hydroxamoyl chloride which is subsequently reacted with 52.8 g (0.44 mol) of methyl vinyl(P-methyl)phosphinate and 61.2 ml (0.44 mol) of triethylamine, and worked up, as described in Example 1(b), the oily product being obtained with a yield of about 50%.

Workup

  1. customthe oily product being obtained with a yield of about 50%

Sources & evidence

ORD record
ord-a497d412dcde41f0bf2239586dc15ebe
Source dataset
uspto-grants-1991_04
Patent number
US05006515

Reaction notes

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