反应详情

温度

-70 °C

LDA (2 M in THF, 53.6 mL, 107 mmol) was added slowly (over 30 min) to a cold (−78° C.) solution of intermediate A (20 g, 77 mmol) in THF (400 mL) (during the addition, the temperature raised to −70° C.). The mixture was stirred for 1 h at −78° C. A solution of 4-cyanobenzaldehyde (14 g, 107 mmol) in THF (100 mL) was added slowly. The reaction mixture was stirred for 30 min at −78° C., allowed to warm to −20° C. over 1 h, quenched by addition of acetic acid (10 mL), diluted with EtOAc/water, and extracted with EtOAc. The organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 1:1), followed by trituration in EtOAc, to provide 20.1 g of the title compound. tR: 0.99 min (LC-MS 2); ESI-MS: 392.2/394.1 [M+H]+ (LC-MS 2); Rf=0.29 (hexane/EtOAc, 1:1).

1. additionduring the addition
2. stirringThe reaction mixture was stirred for 30 min at −78° C.
3. temperatureto warm to −20° C. over 1 h
4. customquenched by addition of acetic acid (10 mL)
5. additiondiluted with EtOAc/water
6. extractionextracted with EtOAc
7. washThe organic extracts were washed with water and brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography (hexane/EtOAc, 1:1)