Tetrabutylammonium Fluoride → 1-Ethynyl-1-(trifluoromethyl)but-3-en-1-yl 4-nitrobenzoate

Participants

Reaction Steps

To a solution of crude 1-(trifluoromethyl)-1-[(triisopropylsilyl)ethynyl]but-3-en-1-yl 4-nitrobenzoate from Step 2 (˜0.755 mmol) in THF (3 mL) at room temperature was added a THF solution of tetrabutylammonium fluoride (1.0 M, 0.906 mL, 0.906 mmol). After 2.5 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 (60 mg). 1H NMR (500 MHz, acetone-d6): 8.44 (d, 2H), 8.29 (d, 2H), 5.94 (m, 1H), 5.29 (d, 1H), 5.21 (d, 1H), 3.74 (s, 1H), 3.27 (m, 2H).

Provenance & Evidence