Water → Diethyl 3-(5-methylpyridin-2-yloxy)benzylphosphonate

HRID 1666404Notes

Reaction equation

HRID 1666404 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1.[CH2:17]([O:19][P:20]([O:24]CC)[O:21][CH2:22][CH3:23])[CH3:18].O>C(OCC)(=O)C>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:4]=[C:3]([CH:16]=[CH:15][CH:14]=2)[CH2:2][P:20](=[O:24])([O:21][CH2:22][CH3:23])[O:19][CH2:17][CH3:18])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 668767842-(3-(Chloromethyl)phenoxy)-5-methylpyridine

Product 1

HCID 86623902Diethyl 3-(5-methylpyridin-2-yloxy)benzylphosphonateYield 59.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

2-(3-(Chloromethyl)phenoxy)-5-methylpyridine (2.0 g, 8.8 mmol) was treated neat with triethylphosphite (1.89 mL, 11 mmol) and heated to 150° C. After 16 h, the reaction mixture was cooled to room temperature and partioned between water and ethyl acetate. The organic layer was separated and the aqueous was extracted again with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by silica gel chromatography (10-75%, EtOAc:CH2Cl2) to afford the title compound (1.75 g, 59% yield) as a thick oil.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous was extracted again with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by silica gel chromatography (10-75%, EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-4ac3228ed30f406e99fe69679c596b99
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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