Ethyl Acetate → HCID 71739072, compound

Participants

Reaction Steps

To a solution of 6-chloropyridin-3-ol (5 g, 38.6 mmol) and ethyl-2-bromo-2-methylpropanoate (6.01 ml, 40.5 mmol) in acetonitrile (50 mL) was added cesium carbonate (27 g, 83 mmol). The material was stirred vigorously for 48 hours. The mixture was taken up in water (100 ml) and ethyl acetate (100 ml) and transferred to a separatory funnel and shaken. The organic phase was collected and the aqueous phase was back extracted with ethyl acetate (2×50 mL). The organic phases were combined, dried (magnesium sulfate), filtered and stripped. The crude material was purified via preparative HPLC (silica gel; 50 g column) eluting with 5-30% ethyl acetate/hexanes to provide the desired product as light white-yellow mobile oil (6.78 g). (M+H)+=244 m/e.

Provenance & Evidence