Sodium periodate → 4-Carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl ester

HRID 29327

Reaktionsgleichung

Reaktionsgleichung von HRID 29327
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=C)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:19].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[CH2:1]([O:3][C:4]([CH:6]1[C:10]([CH3:11])=[C:9]2[C:12](=[C:16]=[O:19])[CH:13]=[CH:14][CH:15]=[C:8]2[O:7]1)=[O:5])[CH3:2]

Komponenten

7

Edukt 2

HCID 23667635Sodium periodateHCID 687131603-Methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester

Produkt 1

HCID 865990284-Carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl esterAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6386tert-ButanolKatalysatorHCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 0.250 g (1.087 mmol) of 3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester (Example 87, Step 1) in 7.5 mL of dioxane and 2.5 mL of water was added 0.272 mL of 2.5 weight % osmium tetroxide in t-butanol (0.022 mmol) and the reaction was stirred for 10 minutes at room temperature, turning yellow-brown in color. Sodium periodate (0.488 g, 2.282 mmol) was then added in several portions over 30 minutes and a white precipitate formed. The reaction was stirred at room temperature for 2 h and then diluted with water and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10) to provide 0.225 g of 4-carbonyl-3-methylbenzofuran-2-carboxylic acid ethyl ester.

Aufarbeitung

  1. customa white precipitate formed
  2. stirringThe reaction was stirred at room temperature for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-937225491e044952839ab9ba28439eeb
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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