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

反応式

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]

参加物

実験手順

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.