Ethyl alpha-oxofuran-2-acetate → (Furan-2-yl)(hydroxy)acetic acid

HRID 2237453

Reaktionsgleichung

Reaktionsgleichung von HRID 2237453
C([O:3][C:4](=[O:12])[C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=[O:6])C.[BH4-].[Na+]>CCO.O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[CH:5]([OH:6])[C:4]([OH:12])=[O:3]

Komponenten

5

Edukt 2

HCID 74230Ethyl alpha-oxofuran-2-acetateHCID 4311764Sodium borohydride

Produkt 1

HCID 86860(Furan-2-yl)(hydroxy)acetic acidAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of the product from step a.) (25 g, 135 mmol) in EtOH (250 ml) was cooled to 0° C. and treated with a solution of NaBH4 (2.5 g, 66 mmol) in H2O (27 ml) for 5 minutes. Next, the reaction mixture was quenched with AcOH (17 ml) and H2O (271 ml) and concentrated to dryness. The crude oil was dissolved in CH2Cl2 (300 ml), washed with brine (2×100 ml), dried (MgSO4) and concentrated providing 17.5 g (70%) of the above subtitle compound, which was carried forward without further purification.

Aufarbeitung

  1. customNext, the reaction mixture was quenched with AcOH (17 ml) and H2O (271 ml)
  2. concentrationconcentrated to dryness
  3. dissolutionThe crude oil was dissolved in CH2Cl2 (300 ml)
  4. washwashed with brine (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8be1c5878a6f405eb4d8bbf1b8bbe68a
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718647B2

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