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

HRID 253985Notes

Reaction equation

HRID 253985 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2ce8e42a330b45c585caf3acaef195c9
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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