反应详情

温度

47.5 °C

A solution of CeCl3 (114.4 g, 0.45 mol) in THF (4 L) was degassed for 1 h and heated to 45-50° C. for 5 h. When the solution was cooled to −10˜−5° C., MeMgCl (193.2 g, 2.6 mol) in THF was added and the mixture was stirred for 1 h at −10˜−5° C. After amide 34 (256 g, 1.3 mol) was charged into the reaction mixture at −10˜−5° C., the mixture was stirred for 5 h at 10-20° C. After the reaction was complete monitored by LCMS, the mixture was quenched by 1M HCl, and then partitioned with water and EtOAc. The organic phase was dried over Na2SO4 and concentrated. The crude residual was further purified by flash chromatography on silica gel (2-10% EtOAc/PE) to give 35 (157 g, 80% yield). 1H NMR (CDCl3, 400 MHz): δ 7.1-6.91 (d, 4H), 3.55 (s, 3H), 2.25 (s, 3H), 2.05 (s, 3H); MS (ESI) m/e [M+H]+: 149.05.

1. temperatureWhen the solution was cooled to −10˜−5° C.
2. stirringthe mixture was stirred for 5 h at 10-20° C
3. customthe mixture was quenched by 1M HCl
4. custompartitioned with water and EtOAc
5. dry with materialThe organic phase was dried over Na2SO4
6. concentrationconcentrated
7. customThe crude residual was further purified by flash chromatography on silica gel (2-10% EtOAc/PE)