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An alternative method for the synthesis of 4-alkyl-2(5H)-furanones is described.Intramolecular carbene addition reaction of alpha-diazo compounds (4) in the presence of rhodium acetate or copper acetylacetonate furnished the bicyclic compounds (5), which were subjected to cyclopropane ring-opening reaction to give the 4-alkyl-4,5-dihydrofuran-2(3H)-ones (6) regioselectively.These compounds (6) were further converted into 4-alkyl-2(5H)-furanones (14) in several steps.Keywords – carbene; intramolecular addition; butenolide; cyclopropanation; ring-opening reaction
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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem