Water → HCID 61720969, compound

Participants

Reaction Steps

A mixture of Example 1D (22.5 g, 68.2 mmol), iron powder (19.0 g, 341 mmol), and ammonium chloride (7.30 g, 136 mmol) in tetrahydrofuran (117 mL), ethanol (117 mL), and water (39 mL) was refluxed at 100° C. for 2 hours. The mixture was cooled just below reflux, and filtered through Celite. The filter cake was washed with warm methanol (3×50 mL). The solution was concentrated under reduced pressure, neutralized to a pH of about 8 with saturated NaHCO3 (150 mL), and extracted with ethyl acetate (3×100 mL). The combined organics were washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered, concentrated, and purified by flash chromatography (silica gel, 0-15% ethyl acetatehexane gradient) to provide the title compound.

Provenance & Evidence