Tetrahydrofuran → (2-Chloropyridin-4-yl)methanol

HRID 15057

Reaktionsgleichung

Reaktionsgleichung von HRID 15057
O1CCCC1.[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=1)[C:10](O)=[O:11]>C(OCC)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:13]=[CH:14][N:15]=1

Komponenten

4

Edukt 2

HCID 8028TetrahydrofuranHCID 2369852-Chloroisonicotinic acid

Produkt 1

HCID 7062237(2-Chloropyridin-4-yl)methanolAusbeute 908,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Borane-dimethyl sulfide complex (14.30 mL, 14.30 mmols) was added to tetrahydrofuran solution of 2-chloroisonicotinic acid (17.56 g, 11.5 mmols) under cooling with ice, and stirred at room temperature for 2.5 days, followed by further an hour's stirring at 50° C. Cooling the reaction liquid to room temperature, ethyl acetate was added, followed by washing with saturated aqueous ammonium chloride solution and saturated brine and drying over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the tide compound (15.0 g, 93%) was obtained.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. waitfollowed by further an hour
  3. stirring's stirring at 50° C
  4. temperatureCooling
  5. customthe reaction liquid to room temperature
  6. washby washing with saturated aqueous ammonium chloride solution and saturated brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. concentrationConcentrating the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3fa492606d864acd8a6b58ac8a2f15f7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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