Abstract
Mephenoxalone (1) was synthesized through a silanizated intermediate prepared from the addition of trimethylsilyl cyanide (TMSCN) to (o-methoxy)phenoxyacetaldehyde (10). Three different methods were established to synthesize this aldehyde. Alkylation of guaiacol with bromoacetaldehyde diethyl acetal, followed by acid hydrolysis of acetal group gave the highest overall yield (49%) for the aldehyde 10. Different reagents as ZnI2, Montmorillonite K10, (+)- Eu(tfc)3 and (+)-Yb(tfc)3 were used in the addition of TMSCN to the aldehyde giving very good yields with all catalysts.
Highlights
Oxazolidinone compounds are important because their broad spectra of pharmacological properties
We reported the synthesis of a bronchodilator blocker Fenspiride (5)[14] and continuing our interest in cyclization reactions using bistrichloromethyl carbonate (BTC or triphosgene) and the addition of trimethylsilyl cyanide to aldehydes,[15] we proposed a new methodology for the synthesis of Mephenoxalone through silanized intermediate
Three different methods were proposed for the synthesis of aldehyde 10 (Scheme 1). 1) Direct alkylation of guaiacol with chloroacetaldehyde under basic conditions with 26% yield
Summary
Oxazolidinone compounds are important because their broad spectra of pharmacological properties. 3) Alkylation of guaiacol with bromoacetaldehyde diethyl acetal, 25% NaOH aqueous solution and HMPA as solvent gave the (o-methoxy)phenoxyacetaldehyde diethyl acetal (9) which was hydrolyzed with HCl in 1,4dioxane to gave the aldehyde 10.16 The overall yield with this method was 49%. The organic phase was dried over Na2SO4, filtered and solvent was evaporated to give an amber liquid (1.7 g, 8.09 mmol, 100% yield).
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