Potassium Hydroxide → 4-Difluoromethoxy-piperidine

Participants

Reaction Steps

4-(difluoromethoxy)piperidine-1-carbaldehyde (17) (2.7 g, 15.07 mmol) and potassium hydroxide (2.96 g, 52.74 mmol) were dissolved in water (40 mL) and stirred vigorously for 3 hours. The reaction was extracted with diethyl ether (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford an orange liquid. The crude product was purified by distillation at 0.70 mBar, collecting fractions that distilled at 25° C. to afford the desired material as a colourless oil (1.100 g, 48.3%); 1H NMR (400.132 MHz, CDCl3) δ 1.50 (1H, s), 1.66-1.57 (2H, m), 1.95-1.89 (2H, m), 2.70-2.64 (2H, m), 3.09 (2H, dt), 4.25-4.19 (1H, m), 6.24 (1H, t).

Provenance & Evidence