3-(Chloromethyl)pyridine hydrochloride → 3-(Diethoxyphosphorylmethyl)pyridine

HRID 52168

Reaction equation

HRID 52168 reaction equation
C([O-])(O)=O.[Na+].Cl.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13]Cl)[CH:8]=1.[CH2:15]([O:17][P:18]([O:22]CC)[O:19][CH2:20][CH3:21])[CH3:16]>>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][P:18](=[O:22])([O:19][CH2:20][CH3:21])[O:17][CH2:15][CH3:16])[CH:8]=1

Participants

4

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 31215Triethyl phosphiteHCID 516892Sodium Bicarbonate

Product 1

HCID 104626053-(Diethoxyphosphorylmethyl)pyridineYield 26.2%

Conditions

Temperature
85 °C

Procedure

To a stirred solution of saturated NaHCO3 was added 3-picolyl chloride hydrochloride (8.2 g, 50 mmol). After gas evolution ended, the mixture was extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated in vacuo. To the resulting residue was added triethylphosphite (8.3 g, 50 mmol) and the neat mixture was stirred and heated at 85° C. overnight. The mixture was cooled and purified by flash column chromotography on silica gel eluting with 5% MeOH--CH2Cl2 to afford 3.0 g of diethyl 3-pyridylmethylphosphonate as a yellow oil.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. temperatureThe mixture was cooled
  5. custompurified by flash column chromotography on silica gel eluting with 5% MeOH

Sources & evidence

ORD record
ord-3480f0481a594e518e4e31c7f928693f
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Linked notes

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