Water → HCID 556336, compound

HRID 866847Notes

Reaction equation

HRID 866847 reaction equation
[Na].[P:2]([O-:9])([O:6][CH2:7][CH3:8])[O:3][CH2:4][CH3:5].CO[N+:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>O1CCOCC1.C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[P:2]([O:6][CH2:7][CH3:8])(=[O:9])[O:3][CH2:4][CH3:5]

Participants

8

Reactant 4

HCID 962WaterHCID 3780918DiethylphosphiteHCID 3807829HCID 3807829, compoundHCID 5360545Sodium

Product 1

HCID 556336HCID 556336, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

To pyridine N-oxide (19 g; 0.2 mole) was added dimethyl sulfate (25.2 g; 0.2 mole) during 30 minutes. The reaction was completed by heating at 100° C. for two hours yielding N-methoxy pyridinium methosulfate. Diethyl sodio phosphonate was prepared by dissolving sodium (4.6 g; 0.2 mole) in a solution of diethyl phosphite (27.6 g; 0.2 mole) in dioxane (100 ml) in an argon atmosphere. The N-methoxy pyridinium quaternary was suspended in toluene by stirring while the diethyl sodio phosphonate solution was added. The reaction flask was cooled to maintain the temperature at 25° - 35° C. After stirring for 11/2 hours, water (100 ml) was added and the organic product isolated by chloroform extraction. Evaporation of the chloroform extract and distillation yielded diethyl pyridine-2-phosphonate with a small amount of diethyl pyridine 4-phosphonate. Yield -- 14g (33%) bp 140° - 8° C./1.5 mm. The presence of the two isomers was established by infrared absorption; 2-isomer 13.3 μ (strong, 4 adjacent hydrogen) and 4 isomer, 12.3 μ (weak, 2 adjacent hydrogen).

Workup

  1. customDiethyl sodio phosphonate was prepared
  2. additionwas added
  3. temperatureThe reaction flask was cooled
  4. temperatureto maintain the temperature at 25° - 35° C
  5. additionwas added
  6. customEvaporation of the chloroform
  7. extractionextract
  8. distillationdistillation

Sources & evidence

ORD record
ord-27c27e3dfb124ee985818223b9a3ad35
Source dataset
uspto-grants-1978_07
Patent number
US04101654

Reaction notes

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