Hydrochloric Acid → Methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylate

HRID 1877038

Reaktionsgleichung

Reaktionsgleichung von HRID 1877038
[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.[CH3:13][O-:14].[Na+].O.Cl>CO>[Br:1][C:2]1[O:6][C:5]([CH2:7][O:14][CH3:13])=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 15534191Methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate

Produkt 1

HCID 68509863Methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate (3.0 g) in methanol (30 mL) was added sodium methoxide (0.8 g) at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture 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 20% ethyl acetate/hexane) to give the title compound (1.9 g, 77%) 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 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3db0976ca935482bae453c50e5a37359
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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