Ethyl Acetate → [5-(4-Chlorophenyl)-2-furyl]methanol

HRID 651039

Reaktionsgleichung

Reaktionsgleichung von HRID 651039
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([O-:14])([O-])=O.[Cs+].[Cs+].[C:17]([O:20][CH2:21][CH3:22])(=O)[CH3:18]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:17]2[O:20][C:21]([CH2:11][OH:14])=[CH:22][CH:18]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 742994-Chlorophenylboronic acid

Produkt 1

HCID 738660[5-(4-Chlorophenyl)-2-furyl]methanolAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The product from Example 11A (1.012 g, 5.72 mmol) in 10 mL of DMF was treated sequentially with PdCl2 (PPh3)2 (401 mg, 0.57 mmol), 4-chlorophenylboronic acid (1.78 g, 11.4 mmol), and Cs2CO3 (3.71 g, 11.4 mmol). The reaction was heated at 80° C. under N2 for 12 hours. The reaction mixture was taken up in ethyl acetate and washed with water (3×) and brine (3×), dried (Na2SO4), filtered, and evaporated to a brown oil that was purified by flash chromatography (50% ethyl acetate/hexanes) to provide 345 mg (35%) the title compound as an oil.

Aufarbeitung

  1. washwashed with water (3×) and brine (3×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated to a brown oil that
  5. customwas purified by flash chromatography (50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8d4bca95abda42dcb233ae63a3d3b30c
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277871B1

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