Potassium Carbonate → HCID 68883501, compound

Participants

Reaction Steps

To a solution of 3-(3-hydroxyphenyl)pyridine (40.91 g, 0.239 mol) in 500 mL dimethylformamide was added potassium carbonate (148.62 g, 1.075 mol) and ethyl-2-bromoisobutyrate (157.8 mL, 1.075 mol). The mixture was heated to reflux under N2 with stirring for 18 h and cooled to ambient temperature. The resultant brown suspension was diluted with 1 L water and extracted with diethyl ether (3×500 mL). The organic phases were combined and dried over anhydrous sodium sulfate, filtered and concentrated to a volume of 1 L. The organic solution was diluted with 1 L water and made acidic with 6N HCl. The layers were separated and the organic phase extracted with 500 mL water. The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (4×500 mL) and the extracts were combined, washed with 500 mL brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield crude 2-methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester as a pale yellow oil which was taken on to the next step without further purification.

Provenance & Evidence