Triethylamine → Methyl 3-(1-naphthyl)-2-isoxazolin-5-yl(P-methyl)phosphinate

HRID 1084795Notes

Reaction equation

[C:1]1([CH:11]=[N:12][OH:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClN1C(=O)CCC1=O.[CH:22]([P:24]([CH3:28])(=[O:27])[O:25][CH3:26])=[CH2:23].C(N(CC)CC)C>>[C:1]1([C:11]2[CH2:23][CH:22]([P:24]([CH3:28])(=[O:27])[O:25][CH3:26])[O:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Reactant 4

HCID 8471Triethylamine

HCID 31398Chlorosuccinimide

HCID 2408011-Naphthalenecarboxaldehyde, oxime

HCID 6454580Methyl methylvinylphosphinate

Product 1

HCID 20062396Methyl 3-(1-naphthyl)-2-isoxazolin-5-yl(P-methyl)phosphinateYield 96.8%

Procedure

39.1 g (0.25 mol) of naphthaldoxime, 36.7 g (0.275 mol) of N-chlorosuccinimide, 33 g (0.275 mol) of methyl vinyl(P-methyl)phosphinate and 38.2 ml (0.275 mol) of triethylamine are reacted as in Example 1 to give 70 g of oily product.

Sources & evidence

ORD record: ord-f9619ce1e0f049b193c8db09d3cb2a25
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006515

Reaction notes

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