反应详情

Dissolve 6-trifluoromethyl-pyridine-3-carboxaldehyde (3.526 g, 20.136 mmol) in THF (50 mL). Add ethylmagnesium bromide (3.0 M in Et2O, 7.38 mL, 22.1 mmol) quickly. Stir 30 minutes. Pour the reaction mixture into a saturated NaHCO3 aqueous solution (100 mL). Extract with EtOAc (3×50 mL). Wash the combined organic extracts with a saturated NaCl aqueous solution (75 mL). Dry the organic extracts over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min) eluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes to give the title compound (2.01 g, 49% yield) as a yellow oil. 1H NMR (400.43 MHz, d6-DMSO) δ 8.66 (d, J=1.6 Hz, 1H), 7.95 (dd, J=1.9, 8.1 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 5.47 (d, J=4.5 Hz, 1H), 4.60 (q, J=5.8 Hz, 1H), 1.65-1.59 (m, 2H), 0.79 (t, J=7.4 Hz, 3H).

1. extractionExtract with EtOAc (3×50 mL)
2. washWash the combined organic extracts with a saturated NaCl aqueous solution (75 mL)
3. dry with materialDry the organic extracts over Na2SO4
4. filtrationfilter
5. customcollect the filtrate
6. concentrationand concentrate the filtrate under reduced pressure
7. customPurify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min)
8. washeluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes