Potassium Carbonate → (E)-3-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-hydroxy-2-methyl-propyl)-phenol (1.00 g, 6.01 mmol), ethyl-2-butynoate (4.00 g, 36.06 mol) and potassium carbonate (0.830 g, 6.01 mmol) in tetrahydrofuran (20 mL) in a sealed tube was heated to 80° C. for 3.75 h. The reaction mixture was then cooled and filtered. The solids were washed with a small amount of tetrahydrofuran and the combined filtrate was collected and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) to afford (E)-3-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester (1.41 g, 84%) as a colorless oil.

Provenance & Evidence