Rapid synthesis of coffee furan by Wilkinson catalyst and its reaction mechanism
The synthetic route of coffee furan is complex and the yield is low.Using 3-thiophenyl alcohol as raw material,the key intermediate 2-acetyl-3-thiophenyl alcohol was obtained,and the coffee furan could be quickly synthesized from this substrate.The effect of the ratio of raw material to acetic anhydride on the yield of the key substrate was investigated,and the reaction mechanism was deduced and veri-fied.The results showed that in the 2-site acetylation reaction of thiophene ring,the optimal ratio of raw material to acetic anhydride was 1.2.Wilkinson catalyst can catalyze the intramolecular cyclation of 2-acetyl-3-thiophenyl carbinol under hydrogenation conditions,and can easily and quickly synthesize cafefu-ran.The intramolecular cyclization reaction of o-hydroxymethylcarbonyl compounds catalyzed by Wilkinson catalyst may undergo intramolecular half-acetone dehydration and catalytic hydrogenation reduction.
fine chemical engineeringWilkinson catalysto-methylol carbonyl compoundscoffee furanintramolecular reduction cyclization
万方数据
维普
