반응 #684947

반응 방정식

4-n-butylbenzylchloride

dimethylformamide

sodium hydride

dimethylformamide

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

→

aforementioned compound

수율 17.2%

1-(4-butylbenzyl)isoquinoline

수율 17.2%

용매

Water

반응 조건

후처리

1. 1
   농축this was concentrated
2. 2
   workup.ADDITIONtoluene and water were added to this residue
3. 3
   세척The toluene layer was washed with water
4. 4
   건조dried over potassium carbonate
5. 5
   농축concentrated
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
   온도this was refluxed for 2 hours
8. 8
   농축After concentration, toluene and water
9. 9
   workup.ADDITIONwere added
10. 10
    세척The toluene layer was washed with water
11. 11
    건조dried over calcium carbonate
12. 12
    농축concentrated
13. 13
    기타The residue was purified by silica gel column chromatography

실험 절차

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).

출처