تفاعل #684947

معادلة التفاعل

4-n-butylbenzylchloride

dimethylformamide

sodium hydride

dimethylformamide

1-cyano-2-benzoyl-1,2-dihydroisoquinoline

→

aforementioned compound

المردود 17.2%

1-(4-butylbenzyl)isoquinoline

المردود 17.2%

المذيبات

Water

ظروف التفاعل

المعالجة

1. 1
   تركيزthis was concentrated
2. 2
   workup.ADDITIONtoluene and water were added to this residue
3. 3
   غسيلThe toluene layer was washed with water
4. 4
   تجفيفdried over potassium carbonate
5. 5
   تركيزconcentrated
6. 6
   workup.ADDITIONTo an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added
7. 7
   درجة الحرارةthis was refluxed for 2 hours
8. 8
   تركيزAfter concentration, toluene and water
9. 9
   workup.ADDITIONwere added
10. 10
    غسيلThe toluene layer was washed with water
11. 11
    تجفيفdried over calcium carbonate
12. 12
    تركيزconcentrated
13. 13
    أخرىThe residue was purified by silica gel column chromatography

الإجراء التجريبي

To a dimethylformamide (1.8 ml) solution of 60% sodium hydride (16 mg, 0.40 mmol), a dimethylformamide (3.6 ml) solution of 1-cyano-2-benzoyl-1,2-dihydroisoquinoline (100 mg, 0.38 mmol) synthesized according to the literature of Org. Synth., VI, 115 (1988), and 4-n-butylbenzylchloride (70 mg, 0.38 mmol) was added dropwise under nitrogen atmosphere at −16° C., and was further stirred at room temperature for 30 minutes. Water was added, this was concentrated, and toluene and water were added to this residue. The toluene layer was washed with water, dried over potassium carbonate, and concentrated. To an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added, and this was refluxed for 2 hours. After concentration, toluene and water were added. The toluene layer was washed with water, then dried over calcium carbonate, and then concentrated. The residue was purified by silica gel column chromatography to give 18 mg of the aforementioned compound of the formula (Ia).

المصدر