Benzyl Alcohol → 5-Formyl-2-furancarboxylic acid benzyl ester

HRID 34097

Reaktionsgleichung

Reaktionsgleichung von HRID 34097
[CH:1]([C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[CH2:24](O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.O>[CH2:24]([O:9][C:8]([C:6]1[O:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)=[O:10])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27937195-Formyl-2-furancarboxylic Acid

Produkt 1

HCID 600347885-Formyl-2-furancarboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

500 mg of 5-formylfuran-2-carboxylic acid was dissolved in 10 mL of tetrahydrofuran, added with 990 μl of triethylamine, cooled to 0° C., and then added with 374 μl of ethyl chloroformate. After stirring at this temperature for 30 minutes, 406 μl of benzylalcohol was added and stirred at room temperature overnight. Adding water to stop the reaction, the solution was extracted with ethyl acetate. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and purified by silica gel column chromatography, to afford 508 mg of the title compound as white crystals.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. customthe reaction
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic phase was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dfac25dd13174f6c8780d2cc80446cf2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

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