Tetrabutylammonium Fluoride → HCID 17785853, compound

Participants

Reaction Steps

A solution of methyl (4-trimethylsilylethynylphenoxy)acetate (20.00 g, 76 mmol) in dichloromethane (400 mL) was deaerated with argon. Tetrabutylammonium fluoride 24.40 g, 91 mmol) was added, and the mixture was stirred for 30 min at ambient temperature. The solution was washed with 10% aqueous citric acid (200 mL), water (5×400 mL), dried over Na2SO4 and concentrated. The residue was dissolved in diethyl ether and passed through a column filled with silica gel. Evaporation of diethyl ether yielded the title compound as a solid (12.63 g, 83%) which was chromatographically and spectroscopically identical with material synthesized previously (Takalo, H., Hemmila, I., Sutela, T. and Latva, M, 1996, Helv. Chim. Acta, 79, 789). Rf (A) 0.50.

Provenance & Evidence