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

HRID 1666397
Notes
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Reaction equation

HRID 1666397 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[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:12]1[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]=[CH:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 668763822-(3-(Chloromethyl)phenoxy)-3-methylpyridine

Product 1

HCID 86623901Diethyl 3-(3-methylpyridin-2-yloxy)benzylphosphonateYield 85.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

2-(3-(Chloromethyl)phenoxy)-3-methylpyridine (3.6 g, 15 mmol) from Step 2 was treated neat with triethylphosphite (3.3 mL, 19.3 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. The residue was purified by silica gel chromatography (30-60%, EtOAc:CH2Cl2) to afford the title compound (4.3 g, 83% 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. customThe residue was purified by silica gel chromatography (30-60%, EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-4b449c9c88d84ec3a351a06a4b177a56
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044052B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes