Tetrabutylammonium Fluoride → 5-(5-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)oxazol-2-yl)-2-isopropoxybenzonitrile

Participants

Reaction Steps

To a solution of 5-(5-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-inden-4-yl)oxazol-2-yl)-2-isopropoxybenzonitrile INT-33 (350 mg, 0.737 mmol) in anhydrous THF (2 mL) was added a 1M solution of tetrabutylammonium fluoride in THF (3.6 mL, 3.6 mmol) at 0° C. The reaction mixture was allowed to stir at room temperature for 16 h before quenching with brine (5 mL). The THF was removed under vacuum, the residue was diluted with water (5 mL), and the aqueous layer was extracted with EA. The combined extracts were washed with brine, dried over MgSO4, and purified by chromatography to afford 220 mg (63%) of 5-(5-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)oxazol-2-yl)-2-isopropoxybenzonitrile 56 as a light yellow solid. LCMS-ESI (m/z) calculated for C22H20N2O3: 360.4; found 343.0 [M−OH]+, tR=2.30 min. 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=2.2 Hz, 1H), 8.26 (dd, J=8.9, 2.2 Hz, 1H), 7.75 (d, J=7.6 Hz, 1H), 7.48 (d, J=7.3 Hz, 1H), 7.42 (t, J=7.6 Hz, 1H), 7.10 (d, J=8.9 Hz, 1H), 5.35 (d, J=4.8 Hz, 1H), 4.78 (dt, J=12.2, 6.1 Hz, 1H), 3.30 (ddd, J=16.4, 8.7, 4.8 Hz, 1H), 3.13-2.94 (m, 1H), 2.64 (dddd, J=13.3, 8.4, 7.1, 4.8 Hz, 1H), 2.17-2.08 (m, 1H), 1.86 (s, 1H), 1.60 (s, 1H), 1.46 (dd, J=13.9, 6.0 Hz, 6H).

Provenance & Evidence