Triethyl phosphite → Diethyl (3-methoxy-isoxazol-5-yl)-methane phosphonate

HRID 54416Notes

Reaction equation

Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=1.[CH2:10]([O:12][P:13]([O:17]CC)[O:14][CH2:15][CH3:16])[CH3:11].ClCC1C=CON=1>>[CH3:9][O:8][C:5]1[CH:4]=[C:3]([CH2:2][P:13]([O:14][CH2:15][CH3:16])(=[O:17])[O:12][CH2:10][CH3:11])[O:7][N:6]=1

Participants

Reactant 3

HCID 31215Triethyl phosphite

HCID 49130253-(Chloromethyl)-1,2-oxazole

HCID 100805435-(Chloromethyl)-3-methoxy-1,2-oxazole

Product 1

HCID 10538561Diethyl (3-methoxy-isoxazol-5-yl)-methane phosphonateYield 56.1%

Procedure

3.8 g 5-chloromethyl-3-methoxy-isoxazole and 6.0 g of triethylphosphite were stirred at 150° C. until complete conversion of the chloromethyl isoxazole (2-8 h). Kugelrohr destillation gave 3.6 g of diethyl (3-methoxy-isoxazol-5-yl)-methane phosphonate. Bp. 160°-165° C./0.3 mm Hg.

Sources & evidence

ORD record: ord-f5490f4ffea645e6a1f3c4add4767df8
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622953

Reaction notes

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