3-Hydroxybenzyl alcohol → 3-[(6-Methyl-2-pyridinyl)oxy]benzenemethanol

HRID 1666388

Reaktionsgleichung

Reaktionsgleichung von HRID 1666388
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:17][C:13]1[N:12]=[C:11]([O:9][C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 1023-Hydroxybenzyl alcoholHCID 10796Cesium carbonateHCID 960902-Fluoro-6-methylpyridine

Produkt 1

HCID 668761143-[(6-Methyl-2-pyridinyl)oxy]benzenemethanolAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-Hydroxymethyl-phenol (3.69 g, 29.7 mmol), 2-fluoro-6-methyl-pyridine (3.00 g, 27 mmol,) and cesium carbonate (9.68 g, 29.7 mmol) were suspended in dimethylsulfoxide (25 mL) and heated to 110° C. After stirring for 16 h, the reaction was partitioned between water (250 mL) and ethyl acetate (250 mL). 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 (10-50%, EtOAc:heptane) to afford the title compound (3.72 g, 64% yield) as an off-white solid.

Aufarbeitung

  1. customthe reaction was partitioned between water (250 mL) and ethyl acetate (250 mL)
  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 (10-50%, EtOAc:heptane)

Quellen und Nachweise

ORD-Eintrag
ord-9ea66b4dec644cb4a889b38fdfe4acff
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

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