反应详情

To a mixture of 4-trifluoromethanesulfonyloxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (10.1 g, 25.9 mmol), 4-fluorophenylzinc bromide solution (0.5 M in THF, 86.3 ml, 43.1 mmol) and 290 ml THF was added tetrakis(triphenylphosphine)palladium(0) (0.83 g, 0.72 mmol) at RT. After stirring for 6 h the reaction was quenched with ice. The mixture was diluted with tert-butyl methyl ether and washed with 2 M aqueous sodium carbonate solution. The aqueous layer was extracted with two portions of tert-butyl methyl ether. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography (heptane/ethyl) gave the title compound as a lightly yellow amorphous residue (6.8 g, 71%).

1. customwas quenched with ice
2. additionThe mixture was diluted with tert-butyl methyl ether
3. washwashed with 2 M aqueous sodium carbonate solution
4. extractionThe aqueous layer was extracted with two portions of tert-butyl methyl ether
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customPurification of the residue by flash chromatography (heptane/ethyl)