Acetic Acid → Ethyl 2-(furan-2-yl)-2-hydroxyacetate

HRID 1518538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518538
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 74230Ethyl alpha-oxofuran-2-acetateHCID 4311764Sodium borohydride

Produkt 1

HCID 11446571Ethyl 2-(furan-2-yl)-2-hydroxyacetateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Ethyl 2-(furan-2-yl)-2-oxoacetate (15.5 g, 92.1 mmol) in ethanol (500 mL) and water (25 mL) at 0° C. was treated with sodium borohydride (1.74 g, 46.05 mmol). The mixture was stirred for 15 minutes, at which point acetic acid (10 mL) was slowly added. After the cessation of gas evolution, water (100 mL) was carefully added, and the reaction mixture was concentrated. The residue was dissolved in methylene chloride and washed with brine. The crude product was dried and concentrated to give ethyl 2-(furan-2-yl)-2-hydroxyacetate as a pale brown viscous oil (11.05 g, 71%) which was used without further purification.

Aufarbeitung

  1. additionwas slowly added
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with brine
  5. dry with materialThe crude product was dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-60956f47bbe242219fbdd8e7eaa0f8a9
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232406B2

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