Triethyl phosphite → 5-Diethylphosphonomethyl-3-methylisoxazole

HRID 1413838Notes

Reaction equation

HRID 1413838 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([CH3:8])[CH:4]=1.[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>C(Cl)(Cl)Cl>[CH2:11]([O:10][P:9]([CH2:2][C:3]1[O:7][N:6]=[C:5]([CH3:8])[CH:4]=1)(=[O:16])[O:13][CH2:14][CH3:15])[CH3:12]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 71314965-(Chloromethyl)-3-methyl-1,2-oxazole

Product 1

HCID 105856985-Diethylphosphonomethyl-3-methylisoxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

445 g of 5-chloromethyl-3-methylisoxazole and 674 g of triethyl phosphite are slowly heated to 150° C. and left at this temperature for 4 hours. After distillation, 546 g (69% of theory) of (3-methylisoxazol-5-yl)-methanephosphonic acid diethyl ester of boiling point 118°-121° C./0.3 mm Hg are obtained. 1H-NMR spectrum (CHCl3, with TMS as internal standard): τ=3.85 (d, J=3 Hz, 1H), 4.17 (m, J=8 Hz, 4H), 6.67 (d, J=22 Hz, 2H), 7.72 (s, 3H), 8.67 (t, J=8 Hz, 6H)

Workup

  1. distillationAfter distillation, 546 g (69% of theory) of (3-methylisoxazol-5-yl)-methanephosphonic acid diethyl ester of boiling point 118°-121° C./0.3 mm Hg
  2. customare obtained

Sources & evidence

ORD record
ord-2328a7143ec24e42a9b5fb95f5334c5c
Source dataset
uspto-grants-1981_02
Patent number
US04251539

Reaction notes

Loading…