Tetrabutylammonium Fluoride → (2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)phenyl)methanol

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To a solution of (2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyloxy)triisopropylsilane (276 mg; 0.602 mmol) in tetrahydrofuran (3.5 mL) was added tetrabutylammonium fluoride (0.62 mL; 0.62 mmol; 1.0 M solution in tetrahydrofuran). Reaction was stirred at room temperature for 1.5 hours. Solvent was evaporated under reduced pressure. The residue was purified by 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-30% ethyl acetate in heptane) to yield 169 mg (92.9%) of the title compound as a colorless gum. MS-GC (El): Calc: 302.3, Found: 302 (M). 1H NMR (400 MHz, CDCl3) δ ppm 7.89 (s, 1H), 7.49 (dd, J=8.30 Hz, 1H), 7.40 (d, J=8.30 Hz, 1H), 5.03 (s, 2H), 3.00 (s, 3H), 2.54 (bs, 1H), 2.23 (m, 2H), 2.04 (m, 2H), 1.88-1.55 (m, 8H).

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