Methyl iodide → Methyl 5-methyl-2-furancarboxylate

HRID 1355905Notes

Reaction equation

HRID 1355905 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].CI>C1COCC1.CN(C=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 747102-Furancarboxylic acid, 5-methyl-

Product 1

HCID 137628Methyl 5-methyl-2-furancarboxylateYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 25.0 g (198 mmol) 5-methyl-2-furoic acid in 160 ml THF and 100 ml DMF were added 110 g (793 mmol) potassium carbonate and 49 ml (787 mmol) methyl iodide and stirring continued for 18 hours at room temperature. The reaction mixture was then filtered and the filtrate concentrated in vacuo. The residue was then partitioned between ether and water, the phases separated, and the aqueous phase further extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Chromatography (hexane then ethyl acetate/hexane 1/9) afforded 27.8 g (100%) methyl 5-methyl-2-furoate as a yellow oil. EI-MS m/e (%): 140 (M+, 44), 109 ([M—OMe]+, 100).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was then partitioned between ether and water
  4. customthe phases separated
  5. extractionthe aqueous phase further extracted with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f580485913a4d0cb23c99e2b002513c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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