Potassium Carbonate → Ethyl 5-(hydroxymethyl)furan-2-carboxylate

HRID 375634Notes

Reaction equation

HRID 375634 reaction equation
C([O:4][CH2:5][C:6]1[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:7]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>O>[OH:4][CH2:5][C:6]1[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 2797254ethyl 5-[(acetyloxy)methyl]-2-furoate

Product 1

HCID 12543487Ethyl 5-(hydroxymethyl)furan-2-carboxylateYield 75.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-acetoxymethyl-2-ethoxycarbonylfuran (Maybridge Chemical Co., Ltd., Tintagel, Cornwall, UK., 0.54 g, 2.5 mmol) and K2CO3 (0.352 g, 2.6 mmol) in 5:1THF/H2O (30 mL), was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-hydroxymethyl-2-carboethoxyfuran (0.32 g) as a yellow liquid which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between CH2Cl2 and saturated aqueous NaHCO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36d1399fc9484d16bde170c70531ca59
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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