Solvent-free Stobbe condensation of furfural1with dimethyl succinate2under anhydrous conditions at room temperature using dry-solid potassium tertiary butoxide gave 3-carbomethoxy, 4-furyl-3-butenoic acid3, which upon methylation followed by Stobbe condensation reaction with different aldehydes and/or ketones under anhydrous conditions at room temperature afforded substituted carbomethoxy acids5a–f. These acid ester products were saponified to the corresponding dicarboxylic acids6a–fwhich are useful in the synthesis of photochromic fulgides.
Condensation reactions O 0120Solvent-Free Stobbe Condensation: A Green Approach. -Stobbe condensation of (I) or (IV) with various aldehydes(II) or ketones (V), resp., can be performed under solvent-free conditions giving higher yields compared to conducting the reaction in tBuOH. -(BANERJEE*, S.; TAYDE, R. A.; SHARMA, B. D.; Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 48 (2009) 6, 882-885; Dep. Chem., Inst. Sci., Nagpur 440 001, India; Eng.) -M. Bohle 42-022
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