Water → HCID 67175826, compound

Participants

Reaction Steps

To a solution of 0.22 g (5.4 mmol) of sodium hydride (60% content) in 3 mL of DMF was added 0.37 g (5.4 mmol) of triazole. Furthermore, a solution of 0.63 g (1.8 mmol) of (2R,3S)-1-chloro-2-(2,4-difluorophenyl)-3-(tert-butyldimethylsilyloxy)butan-2-ol in 10 mL of DMF was added thereto. The resulting reaction mixture was stirred at room temperature for 2 hours and then at 50° C. for 12 hours. Next, 10 mL of water was added to stop the reaction, and extraction was performed with ethyl acetate (30 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain a crude product. The resulting product was purified by column on silica gel to obtain 0.18 g of the title compound (yield: 25%). 1H-NMR (400 MHz, CDCl3) δ: 0.22 (s, 6H), 0.97 (s, 12H), 4.42 (dq, 1H, J=5.9, 1.2 Hz), 4.54 (d, 1H, J=1.4 Hz), 4.81 (d, 1H, J=1.4 Hz), 6.67-6.78 (m, 2H), 7.32-7.38 (m, 1H), 7.71 (s, 1H), 7.96 (s, 1H).

Provenance & Evidence