Tetrabutylammonium Fluoride → HCID 131728525, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tetrabutyl ammonium fluoride (90 g, 0.283 mol) in tetrahydrofuran (250 mL) was added dropwise to a solution of compound of Example 1h (72 g, 0.135 mol) in tetrahydrofuran (350 mL) over a period of 25 min under nitrogen, at 5° C. The reaction mixture was stirred at 5° C. for 30 min. Solvent was removed under reduced pressure and water (250 mL) was added. The solid was filtered and washed with water (2000 mL). The crude product was purified by column chromatography (silica gel, methanol in chloroform) to obtain the title compound. Yield: 37.0 g (87%); 1H NMR (CDCl3, 300 MHz): δ 2.71 (s, 3H, CH3), 3.91 (s, 3H, OCH3), 4.72 (s, 2H, CH2), 7.25 (d, 1H, Ar), 7.33 (d, 1H, Ar), 7.45 (d, 1H, Ar), 8.09 (s, 1H, Ar), 8.46 (s, 1H, Ar); MS: m/e (EI) 352 (M+).

Provenance & Evidence