반응 #9350

반응 방정식

N-bromosuccinimide

Lithium bis (trimethylsilyl) amide

Ethyl 3-pyridylacetate

Chlorotrimethylsilane

→

ethyl 2-bromo-2(3-pyridyl)acetate

용매

H2O

THF

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 20 minutes
2. 2
   workup.STIRRINGto stir
3. 3
   온도warm to room temperature overnight
4. 4
   추출The organic layer was extracted with ethyl acetate
5. 5
   건조The organic phase was dried over sodium sulfate
6. 6
   기타the solvent was evaporated
7. 7
   기타to give a yellow oil
8. 8
   기타The resulting oil was chromatographed on silica gel

실험 절차

Ethyl 3-pyridylacetate (1.0 g, 1.0 eq) was dissolved in THF (50 mL) and cooled to −78° C. Lithium bis (trimethylsilyl) amide (6.66 mL, 1.1 eq) was added to the reaction and stirred for 20 minutes. Chlorotrimethylsilane (1.44 mL, 1.875 eq) was added at −78° C. and stirred for 20 minutes. N-bromosuccinimide (1.09 g, 1.01 eq) was added to the reaction mixture. The reaction mixture was allowed to stir and warm to room temperature overnight. The reaction mixture was diluted with H2O. The organic layer was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and the solvent was evaporated to give a yellow oil. The resulting oil was chromatographed on silica gel using hexanes and ethyl acetate (1:1) to give ethyl 2-bromo-2(3-pyridyl)acetate.

출처