반응 #2235

반응 방정식

Acetyl chloride

methanol

1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

→

title compound

수율 46.6%

3-Methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline

수율 46.6%

용매

DMF

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas then continued for a further 24 h
5. 5
   기타The solvent was removed in vacuo
6. 6
   workup.ADDITIONdichloromethane was added
7. 7
   기타the solid thus formed
8. 8
   여과was filtered off
9. 9
   기타partitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml)
10. 10
    건조The organic phase was dried (magnesium sulphate)
11. 11
    여과filtered
12. 12
    기타the filtrate evaporated in vacuo

실험 절차

Acetyl chloride (0.88 g) was added to methanol (100 ml) with stirring at 0° C. After 10 minutes, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (J. Am. Chem. Soc., 1962, 48, 4487-4494) (2.0 g) was added; the reaction was allowed to warm to room temperature and stirred overnight. DMF (1 ml) was then added and stirring was then continued for a further 24 h. The solvent was removed in vacuo; dichloromethane was added and the solid thus formed was filtered off and partitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml). The organic phase was dried (magnesium sulphate), filtered, and the filtrate evaporated in vacuo to yield the title compound as a pale yellow oil (1.0 g).

출처