Tetrabutylammonium Fluoride → HCID 11345161, compound

Participants

Reaction Steps

To 1.39 g (4.1 mmol) of 2-({2-[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutyl]ethyl}sulfanyl)-1-methyl-1H-imidazole in 10 mL of tetrahydrofuran was added a 1.0 M solution of 4.92 mL (5.33 mmol) of tetrabutylammonium fluoride in tetrahydrofuran and the contents stirred for 16 h. The reaction was concentrated and the residue was poured directly onto a column of silica gel eluting with ethyl acetate:hexane to afford 0.57 g (62%) of (1-{2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]ethyl}cyclobutyl)methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 6.94 (s, 1H), 6.82 (s, 1H), 5.30 (br s, 1H), 3.66 (s, 2H), 3.47 (s, 3H), 2.94 (m, 2H),1.99-1.64 (m, 8H).

Provenance & Evidence