Water → Diethyl 3-(6-methylpyridin-2-yloxy)benzylphosphonate

HRID 1666390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666390
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][CH:10]=[C:9]([CH3:13])[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:9]1[N:8]=[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])[CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 668758892-(3-(Chloromethyl)phenoxy)-6-methylpyridine

Produkt 1

HCID 86623900Diethyl 3-(6-methylpyridin-2-yloxy)benzylphosphonateAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2-(3-(Chloromethyl)phenoxy)-6-methylpyridine (4.0 g, 17 mmol) from Step 2 was treated neat with triethylphosphite (3.67 mL, 21.4 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 (4.7 g, 82% yield) as a thick oil.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-05252a3d0f22414cbd448bff218df469
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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