反应详情

温度

-50 °C

According to Scheme 20: To a solution of 1-(4-chlorobenzyl)-5-(4-acetylphenyl)pyridin-2(1H)-one (1 eq, 0.20 mmol, 80 mg) in THF (5 mL) at −50° C. was added a solution of methyl magnesium bromide (3M, 1.3 eq, 0.30 mmol, 0.04 g) and the reaction stirred at −50° C. for 1 hour. The reaction was quenched at −78° C. with saturated aqueous NH4Cl. The reaction was allowed to warm to room temperature and diluted with AcOEt and the organic phase extracted (×3). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 80/20 and was recrystallized from pentane/Et2O to afford 1-(4-chlorobenzyl)-5-(4-(2-hydroxypropan-2-yl)phenyl)pyridin-2(1H)-one (0.08 mmol, 30 mg, 36%) as a white solid.

1. customThe reaction was quenched at −78° C. with saturated aqueous NH4Cl
2. temperatureto warm to room temperature
3. additiondiluted with AcOEt
4. extractionthe organic phase extracted (×3)
5. dry with materialThe combined organic fractions were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)
9. customwas recrystallized from pentane/Et2O