Hexane → 2-(5-Nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester

Participants

Reaction Steps

To 5-nitro-1H-indole (5.18 g, 31.93 mmol) in acetone (200 ml) at ambient temperature under a nitrogen atmosphere was added cesium carbonate (21.80 g, 67.06 mmol) followed by 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (10.96 g, 35.13 mmol). The resulting dark red mixture was stirred for 5 hours, concentrated in vacuo to a brown powder which was then partitioned between H2O (100 ml) and EtOAc (300 ml). All organics were combined, extracted with brine (250 ml), dried with MgSO4, filtered, and concentrated in vacuo. Gradient SiO2 chromatography (Hexane:EtOAc) afforded 2-(5-nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester as an opaque syrup (5.91 g, 57% yield): MS (ESI) m/z 325, MS (ESI) m/z 323.

Provenance & Evidence