Potassium Carbonate → HCID 72546825, compound

Participants

Reaction Steps

A flame-dried 25 mL two-necked round-bottomed flask equipped with a nitrogen inlet, a septum and a stir bar was charged with compound 19 (0.031 g, 0.094 mmol) and methanol (7 mL). To this solution was added potassium carbonate (0.064 g, 0.48 mmol) followed by the Bestmann-Ohira reagent (0.054 g, 0.28 mmol) in methanol (5 mL). The reaction was stirred at rt overnight. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 2:8). The solution was diluted with ether (10 mL) and then transferred to a separatory funnel containing sat'd aq NaHCO3 solution (15 mL). The layers were separated and the organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel flash column chromatography, eluting with AcOEt/n-hexane 2:8, to provide 0.018 g of the title compound as an orange solid in a 59% yield.

Provenance & Evidence