Tetrabutylammonium Fluoride → HCID 59774877, compound

Participants

Reaction Steps

To a solution of crude 1-cyclopropyl-1-(trifluoromethyl)-3-(triisopropylsilyl)prop-2-yn-1-yl 4-nitrobenzoate from Step 3 (˜8.14 mmol) in THF (30 mL) at room temperature was added a THF solution of tetrabutylammonium fluoride (1.0 M, 9.77 mL, 9.77 mmol). After 1.5 h the reaction mixture was poured in H2O and extracted with EtOAc (3×). The combined organic layers were washed with H2O and brine, dried (Na2SO4) and concentrated. The residue was subjected to chromatography on silica gel (toluene/hexane 40:60 to 60:40) affording the title compound. 1H NMR (400 MHz, acetone-d6): 8.44 (d, 2H), 8.29 (d, 2H), 3.64 (s, 1H), 1.53 (m, 1H), 1.26 (m, 1H), 0.88 (m, 2H), 0.78 (m, 1H).

Provenance & Evidence