Dimethylformamide → 3-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

Participants

Reaction Steps

To 118B (625 mg, 2.46 mmol) in THF (10 mL) and N,N,N′,N″,N″-pentamethyldiethylenetriamine (0.77 mL) was added n-BuLi (1.6M in hexane, 1.77 mL) at −78° C. After stiiring for 45 min at −35° C., DMF (0.94 mL) was added at at −78° C. and the reaction was slowly warmed up to rt. The mixture was stirred at rt for 1 h, diluted with EtOAc. The organic extracts were washed with saturated NaHCO3, brine and dried. The crude product was purified by column chromatography to give 118C (615 mg, 89% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.21 (s, 6H) 1.01 (s, 9H) 1.21 (t, J=7.47 Hz, 3H) 2.59 (q, J=7.47 Hz, 2H) 6.99 (dd, J=7.91, 2.20 Hz, 1H) 7.21-7.27 (m, 1H) 10.30 (s, 1H).

Provenance & Evidence