反应 #684947

反应方程式

4-n-butylbenzylchloride

dimethylformamide

sodium hydride

dimethylformamide

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

→

aforementioned compound

收率 17.2%

1-(4-butylbenzyl)isoquinoline

收率 17.2%

溶剂

Water

反应条件

后处理

1. 1
   浓缩this was concentrated
2. 2
   workup.ADDITIONtoluene and water were added to this residue
3. 3
   洗涤The toluene layer was washed with water
4. 4
   干燥dried over potassium carbonate
5. 5
   浓缩concentrated
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
   温度this was refluxed for 2 hours
8. 8
   浓缩After concentration, toluene and water
9. 9
   workup.ADDITIONwere added
10. 10
    洗涤The toluene layer was washed with water
11. 11
    干燥dried over calcium carbonate
12. 12
    浓缩concentrated
13. 13
    其他The residue was purified by silica gel column chromatography

实验过程

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).

来源