Tetrabutylammonium Fluoride → 3-(2-Benzyloxymethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester

Participants

Reaction Steps

A 250 mL round bottomed flask was charged with 3-[2-benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester (1.03 g, 1.77 mmol), anhydrous THF (60 mL), and then tetrabutylammonium fluoride (5.3 mL, 5.3 mmol, 1.0 M in THF). The reaction mixture was stirred under a nitrogen atmosphere for 1 h, concentrated, and diluted with EtOAc (100 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to give an oil. The crude oil was purified using radial chromatography (EtOAc:hexanes 10:90 to 50:50) to give a white solid (0.52 g, 86%). MS (ES) m/e 343 (M−1).

Provenance & Evidence