تفاعل #2235

معادلة التفاعل

Acetyl chloride

methanol

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

→

title compound

المردود 46.6%

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

المردود 46.6%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto 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
   أخرىThe solvent was removed in vacuo
6. 6
   workup.ADDITIONdichloromethane was added
7. 7
   أخرىthe solid thus formed
8. 8
   ترشيحwas filtered off
9. 9
   أخرىpartitioned between dichloromethane (50 ml) and saturated aqueous sodium hydrogen carbonate solution (50 ml)
10. 10
    تجفيفThe organic phase was dried (magnesium sulphate)
11. 11
    ترشيحfiltered
12. 12
    أخرىthe filtrate evaporated in vacuo

الإجراء التجريبي

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).

المصدر