120211-56-5

Upstream product

• 7332-95-8 3-methyl-1-phenylbutane-1,2-dione 
• 144563-77-9 2-isoptopyl-3-phenyl-5-tributylstannylfuran 
• 144563-84-8 5-acetoxy-5-isopropyl-4-phenyl-2(5H)-furanone 
• 120211-55-4 2,2-Diethoxy-5-isopropylidene-4-phenyl-2,5-dihydro-furan 

Relevant academic research and scientific papers

Oxidative Substitution Reactions of Organostannyl Compounds with Lead Tetraacetate. A Convenient Route to 5-Alkylidene-2(5H)-furanones

5-Substituted 2-tributylstannylfurans which were synthesized by the reaction of corresponding 5-substituted 2-lithiofurans with tribitylstannyl chloride, were treated with two equimolar amounts of lead tetraacetate at room temperature to give corresponding 5-substituted 5-acetoxy-2(5H)-furanones in good yields.The 5-acetoxy-2(5H)-furanone was heated at 80 deg C in acetic acid-acetic anhydride containing a catalytic amount of concentrated sulfuric acid to give 5-alkylidene-2(5H)-furanone in moderate yield.

CONVENIENT SYNTHESIS OF 5-ALKYLIDENE-2(5H)-FURANONES, 2(5H)-FURANONES AND 2-ETHOXYFURANS

Starting from enolizing 1,2-diketones 5 and (2,2-diethoxyvinylidene)triphenylphosphorane (2) or from 5 and (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborate (6) the orthoesters 9 are prepared. 9 can be hydrolyzed under acidic conditions to give 5-alkylidene-2(5H)-furanones 10.Reaction of 1,2-hydroxyketones 11 and (2,2-ditehoxyvinylidene)triphenylphosphorane (2) via Michael addition and Wittig reaction yields orthoesters 15, which can be hydrolyzed to give 2(5H)-furanones 16 and 2-ethoxyfurans 17 respectively.A considerable variation of the substitens (R4)can be achieved starting from 11 and (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborates 12.