反応 #65920

反応方程式

sodium hydroxide

2-cycloheptylcarbamoylmethylfluorene

methanol

hydrochloric acid

→

2-cycloheptylaminoethylfluorene

収率 66.0%

溶媒

chloroform

tetrahydrofuran

chloroform

反応条件

後処理

1. 1
   workup.ADDITIONfollowed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-
2. 2
   温度cooling
3. 3
   workup.ADDITIONwas added with ice-
4. 4
   温度cooling
5. 5
   温度cooling
6. 6
   温度The mixture was refluxed again for 30 minutes
7. 7
   温度The reaction mixture was then cooled with ice
8. 8
   ろ過the resulting solid was recovered by filtration
9. 9
   洗浄washed with ether
10. 10
    その他The solid matter thus obtained
11. 11
    その他dried
12. 12
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

実験手順

In dry tetrahydrofuran (30 ml) was dissolved 2-cycloheptylcarbamoylmethylfluorene (1.9 g) followed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-cooling. The mixture was then refluxed for 4 hrs, at the end of which time methanol (0.72 ml) was added with ice-cooling. The mixture was stirred at room temperature for 30 minutes, followed by addition of concentrated hydrochloric acid (1.8 ml) with ice-cooling. The mixture was refluxed again for 30 minutes. The reaction mixture was then cooled with ice and the resulting solid was recovered by filtration and washed with ether. The solid matter thus obtained was dissolved in chloroform and the solution was alkalinized with aqueous sodium hydroxide solution. The chloroform layer was taken and dried and the solvent was distilled off under reduced pressure to give 2-cycloheptylaminoethylfluorene (1.2 g).

出典