Methyl 5-(chloromethyl)-2-furoate → Methyl 5-methyl-2-furancarboxylate

HRID 1421817Notes

Reaction equation

HRID 1421817 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 75065Methyl 5-(chloromethyl)-2-furoate

Product 1

HCID 137628Methyl 5-methyl-2-furancarboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 5-chloromethyl-2-furoate (5.0 g, 28.7 mmol) in ethyl acetate (40 ml) was hydrogenated over 10% palladium on charcoal (50 mg) for 3 h. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were concentrated in vacuo and the residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexane to yield the title compound as a colourless oil (3.78 g, 94%); νmax (CH2Cl2) 1725, 1534, 1522, 1437 and 1311 cm-1 ; δHCDCl3, 90 MHz) 2.38 (3H, s), 3.86 (3H, s), 6.12 (1H, br d, J 4 Hz) and 7.07 (1H, d, J 4 Hz). [Mass spectrum: M+ (140)].

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. customthe residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6f28a86c61af4687a0a0d757bbca4f14
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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