Tetrahydrofuran → HCID 22633969, compound

Participants

Reaction Steps

To a 0° C. solution of 1.015 g (8.60 mmol) of potassium t-butoxide suspended in 10 mL of dry THF was added a solution of 1.40 g (8.60 mmol) of 4-but-2-ynyloxy-phenol, dissolved in 30 mL of THF/DMF (5:1). The reaction was stirred at room temperature for 10 minutes and then recooled to 0° C. followed by the addition of 0.66 mL (9.46 mmol) of neat •-propiolactone. The resulting mixture was stirred overnight at room temperature and then concentrated in vacuo. The residue was diluted with ethyl acetate and extracted with saturated sodium bicarbonate solution. The alkaline aqueous extracts were acidified to pH2 with concentrated HCl solution and the precipitated solid was collected by filtration, washed with water and dried in vacuo to provide 0.089 g of the carboxylic acid as a black solid; m.p. 88-92° C. Electrospray Mass Spec: 232.9 (M−H)−

Provenance & Evidence