Tetrabutylammonium Fluoride → HCID 178525696, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (0.12 ml) was added to a stirred solution of 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanecarboxylic acid (22 mg) in tetrahydrofuran (1 ml) at room temperature under argon. After 24 hr, the reaction mixture was partitioned between ethyl acetate (30 ml) and water (30 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 7:1 v/v, <1% acetic acid) to give the title compound as an orange solid (10 mg, 89%). δH(CD3OD) 1.40-1.65 (4H, m), 1.88-1.95 (2H, m), 2.06-2.14 (2H, m), 2.35 (1H, tt), 2.82 (1H, it), 6.25-6.30 (2H, m), 6.90 (1H, d); m/z (ES−) 235 (M−H)−.

Provenance & Evidence