反应详情

To a solution of 4,4,4-trifluoro-3-hydroxy-3-methyl-1-[4-(pyrid-4-ylsulfonyl)phenyl]but-1-yne (0.32 g, 0.90 mmol) in dry tetrahydrofuran (5 mL) was added lithium aluminum hydride (44.4 mg, 1.17 mmol) portionwise over 1 minute and the suspension was stirred for 1 hour. The crude reaction mixture was treated sequentially with water (0.4 mL), 2N sodium hydroxide (0.4 mL), and water (1 mL). This mixture was stirred for 10 minutes, filtered through diatomaceous earth with ethyl acetate. The combined washings and filtrate were separated and the aqueous phase was extracted with ethyl acetate. The organic extracts were dried and evaporated. The crude oil was purified by chromatography with ethyl acetate:dichloromethane as the eluent (1:5) to yield the title compound as a white solid (60 mg, 18%); mp 168°-171° C.; NMR (CDCl3): 1.59 (s,3, CH3), 2.43 (s,1, OH), 6.41 (d,1, J=15.9, vinylic), 6.93 (d,1, J=15.9, vinylic), 7.56 (d,2, J=5.9, Ar), 7.76 (d,2, J=5.9, Ar), 7.93 (d,2, J=8.3, Ar), 8.82 (d,2, J=5.9, Ar); MS (EI): m/z=357(M+). Analysis for C16H14F3NO3S: Calculated: C, 53.77; H, 3.95; N, 3.92; Found: C, 53.41; H, 4.05; N, 3.84.

1. customThe crude reaction mixture
2. stirringThis mixture was stirred for 10 minutes
3. filtrationfiltered through diatomaceous earth with ethyl acetate
4. customThe combined washings and filtrate were separated
5. extractionthe aqueous phase was extracted with ethyl acetate
6. customThe organic extracts were dried
7. customevaporated
8. customThe crude oil was purified by chromatography with ethyl acetate