Water → 5-(Benzyloxy)-2-fluoropyridine

HRID 1621774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1621774
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 27631086-Fluoropyridin-3-ol

Produkt 1

HCID 665998445-(Benzyloxy)-2-fluoropyridineAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-5-hydroxypyridine (Combi-block) (1.00 g, 8.84 mmol) in DMF (12 mL) was treated with sodium hydride, 60% dispersion in mineral oil (Alfa-Aesar) (0.88 g, 22.1 mmol) at rt under N2. After stirring for 40 min, benzyl chloride (Aldrich) (3.05 mL, 26.5 mmol) and tetrabutylammonium iodide (Aldrich) (0.33 g, 0.88 mmol) were added, and the reaction mixture was stirred for a further 2 h. Water (2 mL) was added to quench the reaction, and the reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic extracts were washed with sat. NaHCO3, brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (120 g, 10% to 20% actone in hexanes) to give the product as a colorless liquid (1.32 g). m/z (ESI, +ve ion) 204.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.91 (br. s., 1H); 7.32-7.51 (m, 6H); 6.86 (dd, J=8.84, 3.29 Hz, 1H); 5.10 (s, 2H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for a further 2 h
  2. customto quench
  3. customthe reaction
  4. customthe reaction mixture was partitioned between EtOAc and sat. NaHCO3
  5. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
  6. washThe combined organic extracts were washed with sat. NaHCO3, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (120 g, 10% to 20% actone in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7acc356913eb4060984f96bb192c4918
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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