Water → (2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)phenyl)methanol

To a solution of (2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane (1.13 g, 2.4 mmol) in THF (5 mL) at room temperature was added TBAF in THF (1.0 M, 4.8 mL, 4.8 mmol). The mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography over 25+M Biotage silica column (eluted with 0-30% ethyl acetate in heptane) to afford the title compound (633.9 mg, 88%). 1H NMR (400 MHz, CDCl3) δ ppm 0.91-1.27 (m, 6H) 1.63-1.70 (m, 3H) 1.72-1.81 (m, 1H) 2.07 (d, J=12.86 Hz, 1H) 2.33-2.42 (m, 1H) 3.18 (s, 3H) 4.10 (d, J=7.88 Hz, 1H) 4.78 (dd, J=5.81, 3.32 Hz, 2H) 7.43 (d, J=7.88 Hz, 1H) 7.55 (d, J=8.30 Hz, 1H) 7.69 (s, 1H).

1. extractionthe mixture was extracted with ethyl acetate
2. washCombined organic layers were washed with brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was purified by chromatography over 25+M Biotage silica column (eluted with 0-30% ethyl acetate in heptane)

ORD record

ord-5fafb6bc74174aba9782d556b7a48049

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919506B2