반응 #322777

반응 방정식

sulfuric acid

5,6,7-Trimethylquinoline-8-carboxaldehyde n-Butyl lithium

8-bromo-5,6,7-trimethylquinoline

N-formylpiperidine

potassium carbonate

→

5,6,7-trimethylquinoline-8-carboxaldehyde

용매

THF

THF

반응 조건

후처리

1. 1
   온도the mixture was warmed to room temperature
2. 2
   추출was then extracted with ether
3. 3
   건조The dried (MgSO4) organic fraction
4. 4
   기타was evaporated
5. 5
   기타the residue was purified by column chromatography over alumina with carbon tetrachloride/dichloromethane (1:1 v/v) elution

실험 절차

5,6,7-Trimethylquinoline-8-carboxaldehyde n-Butyl lithium (2.1 equiv; 1.55M in hexane) was added slowly to a suspension of 8-bromo-5,6,7-trimethylquinoline (4.2 g) in anhydrous THF (40 ml) under nitrogen at -90° C. After 3 hr a solution of N-formylpiperidine (2.1 equiv) in anhydrous THF (10 ml) was added and the mixture was warmed to -40° C. over ca. 2 hr. A dilute sulfuric acid solution (1N; 20 ml) was added and the mixture was warmed to room temperature. The mixture was made basic by the addition of potassium carbonate and was then extracted with ether. The dried (MgSO4) organic fraction was evaporated and the residue was purified by column chromatography over alumina with carbon tetrachloride/dichloromethane (1:1 v/v) elution to give 5,6,7-trimethylquinoline-8-carboxaldehyde as a pale yellow solid, mp 162° C. Pmr spectrum (CDCl3 ; δ in ppm): 2.48 (3H,s); 2.68 (3H,s); 2.74 (3H,s); 7.43-8.96 (3H,m); 11.61 (1H,s).

출처