tert-Butyldimethylsilyl trifluoromethanesulphonate → 8-(1-((Tert-butyldimethylsilyl)oxy)vinyl)quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(quinolin-8-yl)ethanone (200 mg, 1.169 mmol) and TEA (0.2 mL, 1.520 mmol) in DCM (2 mL) at 0° C. was added TBSOTf (339 mg, 1.286 mmol), and the resulting mixture was stirred at 0° C. for 1 h. The mixture was diluted with sat. aq. NaHCO3 and extracted with EtOAc (2×5 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield crude 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)quinoline (300 mg) as a black solid (used without further purification): 1H NMR (400 MHz, DMSO-d6): δ 9.07 (1H, dd, J=1.6 Hz & 2.4 Hz), 8.23 (1H, dd, J=2 Hz & 6.4 Hz), 8.00 (1H, dd, J=1.6 Hz & 5.6 Hz), 7.84 (1H, dd, J=1.6 Hz & 6.8 Hz), 7.59 (1H, t, J=7.6 Hz), 7.49 (1H, dd, J=4 Hz & 4.4 Hz), 5.43 (1H, s), 5.02 (1H, s), 1.01 (9H, s), 0.20 (6H, s). m/z (ESI, +ve) 285.9 (M+H)+.

Provenance & Evidence