반응 #81497

반응 방정식

ethyl 3-(3quinolyl)propionate

LAH

Rochelle salt

→

3-(3-hydroxypropyl)quinoline

수율 85.0%

용매

ether

반응 조건

후처리

1. 1
   온도to warm
2. 2
   workup.STIRRINGstirred at 20° C. for 3 h
3. 3
   추출The mixture was extracted with methylene chloride
4. 4
   건조the organic layer was dried over sodium sulfate
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by chromatography on silica (10 cm column, ethyl acetete/hexane, 1/2-5/1; methylene chloride/acetone, 2/1-1/4)

실험 절차

To a cooled (0° C.) solution of ethyl 3-(3quinolyl)propionate (1.01 g, 4.4 mmol) in 20 ml of ether was added 2.6 ml (2.6 mmol) of 1M LAH solution at 0° C. After stirring at 0° C. for 15 min, the mixture was allowed to warm and stirred at 20° C. for 3 h, and Rochelle salt (equiv) was added. The mixture was extracted with methylene chloride, and the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica (10 cm column, ethyl acetete/hexane, 1/2-5/1; methylene chloride/acetone, 2/1-1/4) to afford 700 mg (85%) of 3-(3-hydroxypropyl)quinoline, as a thick oil. 3-[3-[4-(5-Trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-quinoline (I, Q=3-quinolyl Y=1,3-propylene, R1,R2 =3,5-dimethyl, R3 =5-trifluoromethyl-1,2,4-oxadiazol-3-yl)

출처