反应详情

温度

55 °C

To a solution of 0.30 g (1.4 mmol) of 3-iodo-1-methyl-1H-pyrazole in 3 mL of anhydrous THF was added a solution of 0.82 g (1.8 mmol) of benzyl 2-(tributylstannyl)acrylate from step B above in 1 mL of anhydrous THF, 0.18 g (0.15 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.14 g (1.4 mmol) of copper (I) chloride. The reaction mixture was heated to 55° C. for 12 h, cooled and evaporated to dryness under reduced pressure. The residue was dissolved in 10 mL of a 1:1 mixture of hexane and EtOAc then filtered through a pad of Celite®. The pad was washed with 15 mL of a 1:1 mixture of hexane and EtOAc and the combined filtrates were evaporated to dryness. The crude residue was purified by silica gel chromatography eluting with a 0-80% EtOAc in hexanes gradient to afford the title compound as a colorless oil (0.23 g, 66%). LC-MS: m/z (ES) 265 (M+Na)+.

1. temperaturecooled
2. customevaporated to dryness under reduced pressure
3. dissolutionThe residue was dissolved in 10 mL of a 1:1 mixture of hexane and EtOAc
4. filtrationthen filtered through a pad of Celite®
5. washThe pad was washed with 15 mL of a 1:1 mixture of hexane and EtOAc
6. customthe combined filtrates were evaporated to dryness
7. customThe crude residue was purified by silica gel chromatography
8. washeluting with a 0-80% EtOAc in hexanes gradient