反应详情

温度

-78 °C

To a pre-cooled −78° C. stirred solution of trimethyl (2-methylbut-3-yn-2-yloxy) silane (5.0 g, 0.03 mol) in dry THF (150 mL), n-BuLi (23.82 mL, 0.03 mol, 1.6 M in hexane) was added dropwise over a period of 10 minutes under an inert atmosphere. The reactions was stirred for 30 minutes at −78° C. and then a solution of N-methoxy-N-methylisonicotinamide (6.34 g, 0.03 mol) in dry THF (30 mL) was added to the reaction mixture and stirring was continued for an additional 40 min at −78° C. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and finally concentrated in vacuo to obtain a residue. The residue was purified via silica gel column chromatography eluting with 5% EtOAc in hexanes to afford 4-methyl-1-(pyridin-4-yl)-4-(trimethylsilyloxy) pent-2-yn-1-one (2.2 g, 27%) as oil.

1. additionwas added dropwise over a period of 10 minutes under an inert atmosphere
2. stirringstirring
3. waitwas continued for an additional 40 min at −78° C
4. customThe reaction mixture was quenched with a saturated NH4Cl solution
5. extractionextracted with EtOAc (2×100 mL)
6. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationfinally concentrated in vacuo
10. customto obtain a residue
11. customThe residue was purified via silica gel column chromatography
12. washeluting with 5% EtOAc in hexanes