反応 #684947

反応方程式

4-n-butylbenzylchloride

dimethylformamide

sodium hydride

dimethylformamide

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

→

aforementioned compound

収率 17.2%

1-(4-butylbenzyl)isoquinoline

収率 17.2%

溶媒

Water

反応条件

後処理

1. 1
   濃縮this was concentrated
2. 2
   workup.ADDITIONtoluene and water were added to this residue
3. 3
   洗浄The toluene layer was washed with water
4. 4
   乾燥dried over potassium carbonate
5. 5
   濃縮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
   濃縮After concentration, toluene and water
9. 9
   workup.ADDITIONwere added
10. 10
    洗浄The toluene layer was washed with water
11. 11
    乾燥dried over calcium carbonate
12. 12
    濃縮concentrated
13. 13
    その他The residue was purified by silica gel column chromatography

実験手順

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).

出典