An Efficient Process for the Synthesis of Novel 1-[(2,7-Dichloro-9-(4-chlorobenzylidene)-9H-fluoren-4-yl]-2-(methylselanyl)ethanol with Excellent HPLC Purity

Abstract

A convenient, commercial and simple process was developed for the synthesis of 1-[2,7-dichloro-9-(4-chlorobenzylidene)-9H-fluoren-4-yl]-2-(methylselanyl)ethanol. 2-(2,7-dichloro-9H-fluoren-4-yl)oxirane was converted to 1-(2,7-dichloro-9H-fluoren-4-yl)-2-(methylselanyl)ethanol in presence of dimethyl diselenide and sodium borohydride and consequently converted to 1-[2,7-dichloro-9-(4-chlorobenzylidene)-9H-fluoren-4-yl]-2- (methylselanyl)ethanol via Knoevenagel condensation with 4-chlorobenzaldehyde in presence of sodium hydroxide in reasonably good yield and purity.

Keywords:

• Diselenides
• epoxides
• Knoevenagel condensation
• ring opening

Acknowledgement

One of the authors, Divyaraj Puthran, is grateful to the management of Solara Active Pharma Sciences Ltd., New Mangalore for supporting the research work and Central Instrumentation Facility, MIT, Manipal for providing IR, ¹H NMR and ¹³C NMR spectral facilities.