Methyl iodide → Methyl (furan-2-yl)(oxo)acetate

HRID 1003963Notes

Reaction equation

HRID 1003963 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[O:9]=[CH:10][C:11]([OH:13])=[O:12].[O:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1>CN(C)C=O>[O:9]=[C:10]([C:15]1[O:14][CH:18]=[CH:17][CH:16]=1)[C:11]([O:13][CH3:3])=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86755299HCID 86755299, compound

Product 1

HCID 118422Methyl (furan-2-yl)(oxo)acetateYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (3.34 ml) was added to a stirred mixture of potassium carbonate (7.4 g) and furan α-oxoacetic acid (5 g) (Fluka) in dimethylformamide (70 ml). The mixture was stirred for 3 days and then partitioned between ethyl acetate and water. The organic phase was washed three times with water, then brine, dried over magnesium sulphate and evaporated. The product (2.1 g) was isolated by column chromatography using gradient elution (Kieselgel:3:1 going to 1:1 hexane:ethyl acetate. δH (250 MHz, CDCl3), 3.96 (3H, s), 6.62-6.65 (1H, m), 7.75-7.78 (2H, m).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed three times with water
  3. dry with materialbrine, dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-b0218245faca4d45b9592e44cb5a4d3f
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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