Hydrochloric Acid → Methyl 5-bromo-2-(ethoxymethyl)furan-3-carboxylate

HRID 1877041

Reaktionsgleichung

Reaktionsgleichung von HRID 1877041
[Br:1][C:2]1[O:6][C:5]([CH2:7]Br)=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.[O-:13][CH2:14][CH3:15].[Na+].C(O)C.O.Cl>C(O)C>[Br:1][C:2]1[O:6][C:5]([CH2:7][O:13][CH2:14][CH3:15])=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 15534191Methyl 5-bromo-2-(bromomethyl)furan-3-carboxylateHCID 23706232Ethanol sodium ethoxide

Produkt 1

HCID 68515316Methyl 5-bromo-2-(ethoxymethyl)furan-3-carboxylateAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate (4.5 g) in ethanol (50 mL) was added 20% sodium ethoxide-ethanol solution (7.8 g) at 0° C., and the mixture was stirred at 0° C. for 2 hr and at room temperature overnight. The reaction was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 15% ethyl acetate/hexane) to give the title compound (2.8 g, 67%) as an oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 15% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e39c62e7d8ed4c7787a016bcd89160a4
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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