(E)-2-(6-fluoro-1-indanylidene)acetamide → (Z)-2-(6-fluoro-1-indanylidene)acetamide

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Reaction Steps

A solution of (E)-2-(6-fluoro-1-indanylidene)acetamide (20 g,104.6 mmol) in dichloromethane:methanol(3:1) (1000 ml) was irradiated by an Canrad-Hanovia quartz, mercury-vapor photochemical immersion lamp, 450 wattts (Ace Glass, 7825-35) for 0.5 h. The volatiles were removed by spin evaporation in vacuo to give a beige residue. This residue was chromatographed on Silica Gel 60 using a step gradient going from ethyl acetate: hexanes(1:1) to ethyl acetate:ethanol(1:1). Fractions containing (Z)-2-(6-fluoro-1-indanylidene)acetamide were combined and concentrated by spin evaporation in vacuo. The resulting solid was slurried in hexanes to give 7.2 g (37%) of (Z)-2-(6-fluoro-1-indanylidene)acetamide as a white crystalline solid, m.p.,175°-177 ° C.;

Provenance & Evidence