Tetrabutylammonium Fluoride → HCID 11493084, compound

Participants

Reaction Steps

[3-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-(1-isobutyl-1H-indazol-3-yl)-methanone (0.650 g, 0.0012 mol) was dissolved in dry THF (1 mL) in a glass vial. The vial was cooled to −78 C in a dry ice/acetone bath. TBAF (1.8 mL of a 1 M soln., 0.0018 mol) was added. The vial was removed from the bath and stirred until a dark yellow color persisted (approx. 1 minute). The vial was placed back in the bath and the progress of the reaction was followed by TLC. When complete, the reaction was quenched with aqueous HCl (1-2N), adsorbed on a small plug of silica gel, and chromatographed with hexane/ethyl acetate (10:1) to give the desired product.

Provenance & Evidence