반응 #1062008

반응 방정식

methyl benzoate

2-cyano-6-methylpyridine

lithium bis(trimethylsilyl)amide

→

subtitle compound

수율 13.7%

6-cyano-2-(2-oxo-2-phenylethyl)-pyridine

수율 13.7%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도The mixture was cooled to 0° C.
3. 3
   기타quenched with 1N HCl
4. 4
   추출extracted with ethyl acetate (3×)
5. 5
   기타The organic layer was separated
6. 6
   기타dried
7. 7
   농축concentrated
8. 8
   기타to give crude material which
9. 9
   기타was purified by chromatography on silica gel

실험 절차

To a solution of 2-cyano-6-methylpyridine (9.7 g, 0.082 mol) in 400 ml of dry THF at -78° C. was added dropwise 90 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF. After stirring for 30 minutes a solution of methyl benzoate (30 ml, 0.245 mol) in 50 ml of THF was added dropwise. The resulting mixture was allowed to warm to room temperature and stirred overnight. The mixture was cooled to 0° C., quenched with 1N HCl, made basic with 15% NaOH solution, and extracted with ethyl acetate (3×). The organic layer was separated, dried, and concentrated to give crude material which was purified by chromatography on silica gel to give 2.5 g of the subtitle compound.

출처