Hydrochloric Acid → ethyl 2-(4-oxo-4H-pyran-3-yloxy)acetate

HRID 426992

Reaction equation

HRID 426992 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][CH:3]=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C>[O:8]=[C:7]1[CH:6]=[CH:5][O:4][CH:3]=[C:2]1[O:1][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 681293-Hydroxy-4H-pyran-4-one

Product 1

HCID 20544471ethyl 2-(4-oxo-4H-pyran-3-yloxy)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-hydroxy-4H-pyran-4-one (1.12 g), ethyl 2-bromoacetate (1.7 g) and potassium carbonate (1.4 g) in ethanol (30 ml) was stirred at 67° to 70° C. for 75 minutes. The reaction mixture was allowed to stand at room temperature. An insoluble substance was filtereed off, and the filtrate was adjusted to pH 4 to 5 with conc. hydrochloric acid and the ethanol was removed. To the residue was added ethyl acetate, and the resultant mixture was washed with an aqueous solution saturated with sodium chloride and dried over magnesium sulfate. After removal of the solvent, the residue was chromatographed on silica gel (15 g) with an eluent (ethyl acetate:benzene= 1:5) to give crystals of ethyl 2-(4-oxo-4H-pyran-3-yloxy)acetate, mp 58° to 60° C.

Workup

  1. customto stand at room temperature
  2. customthe ethanol was removed
  3. additionTo the residue was added ethyl acetate
  4. washthe resultant mixture was washed with an aqueous solution saturated with sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent
  7. customthe residue was chromatographed on silica gel (15 g) with an eluent (ethyl acetate:benzene= 1:5)

Sources & evidence

ORD record
ord-f78b6c3c67fc47a6ab5ccbc8478235ff
Source dataset
uspto-grants-1979_10
Patent number
US04172198

Linked notes

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