Ethyl alpha-oxofuran-2-acetate → alpha-Hydroxy-2-furanacetic acid

HRID 2237453Notes

Reaction equation

HRID 2237453 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 86860alpha-Hydroxy-2-furanacetic acidYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8be1c5878a6f405eb4d8bbf1b8bbe68a
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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