反応 #2235

反応方程式

Acetyl chloride

methanol

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

→

title compound

収率 46.6%

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

収率 46.6%

溶媒

DMF

反応条件

後処理

1. 1
   温度to 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
   その他The solvent was removed in vacuo
6. 6
   workup.ADDITIONdichloromethane was added
7. 7
   その他the solid thus formed
8. 8
   ろ過was filtered off
9. 9
   その他partitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml)
10. 10
    乾燥The organic phase was dried (magnesium sulphate)
11. 11
    ろ過filtered
12. 12
    その他the filtrate evaporated in vacuo

実験手順

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).

出典