反应详情

温度

0 °C

To a stirred suspension of CeCl3 (4.7 grams, 19.0 mmole) in tetrahydrofuran (30 ml) at 0° C. was added dropwise 3.0 M methyl magnesium chloride (6.0 ml, 19.0 mmole). The mixture was stirred at 0° C. for 45 minutes and 4-Acetyl-2-fluoro-benzonitrile (2.5 grams, 15.0 mmole) in tetrahydrofuran (20 ml) was added dropwise. The mixture was stirred at 0° C. for 1 hour and quenched with 5 ml 2 N acetic acid added dropwise. The mixture was poured into 200 ml water, acidified to pH 2 with 2 N acetic acid and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate and concentrated to give an oil which was purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent to give an oil (1.95 g). MW 179.21; MS (m/e) 179 (M+).

1. stirringThe mixture was stirred at 0° C. for 1 hour
2. customquenched with 5 ml 2 N acetic acid
3. additionadded dropwise
4. additionThe mixture was poured into 200 ml water
5. extractionextracted with ethyl acetate
6. washThe combined extracts were washed with water and brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated
9. customto give an oil which
10. customwas purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent