Methyl 4-(hydroxymethyl)-5-methylfuran-2-carboxylate → 5-(Methoxycarbonyl)-2-methylfuran-3-carboxylic acid

HRID 2266792Notes

Reaction equation

HRID 2266792 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][O:15][C:16]([C:18]1[O:19][C:20]([CH3:25])=[C:21]([CH2:23][OH:24])[CH:22]=1)=[O:17]>CC(C)=O.C(OCC)C>[CH3:14][O:15][C:16]([C:18]1[O:19][C:20]([CH3:25])=[C:21]([C:23]([OH:3])=[O:24])[CH:22]=1)=[O:17]

Participants

5

Reactant 2

HCID 58824163Methyl 4-(hydroxymethyl)-5-methylfuran-2-carboxylateHCID 131709961Jones' reagent

Product 1

HCID 184446775-(Methoxycarbonyl)-2-methylfuran-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

Jones' reagent (Prepared according to Fieser and Fieser, Reagents for Organic Synthesis, Volume 1, page 142, 1967) was added drop-wise to a stirred solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (100 mg) in acetone (10 mL) until the orange colouration just remained. Stirring was continued for a further 5 hours then the reaction mixture was diluted with diethyl ether (20 mL) and filtered. The filtrate was dried and concentrated in vacuo to afford compound 23 as a buff coloured solid.

Workup

  1. filtrationfiltered
  2. customThe filtrate was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1b8d5202d00423ea911c7037a256eea
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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