反応 #1448

反応方程式

benzyl cyanide

1,4-dibromobutane

water

ethyl acetate

→

1-phenylcyclopentanecarboxylic acid

溶媒

sodium hydride

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGagain stirred for 16 hours at room temperature
2. 2
   その他the resulting organic layer was separated
3. 3
   洗浄washed with a saturated sodium chloride aqueous solution
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   その他After removing the solvent
6. 6
   workup.DISTILLATIONby distillation under a reduced pressure
7. 7
   workup.ADDITIONthe resulting hexane eluate was mixed with 45 ml of sulfuric acid
8. 8
   workup.WAITsubjected to 24 hours
9. 9
   温度of heating
10. 10
    温度under reflux
11. 11
    温度After cooling down to room temperature
12. 12
    workup.ADDITIONthe reaction solution was mixed with ice water and ethyl acetate
13. 13
    その他to separate water layer which
14. 14
    workup.ADDITIONwas subsequently mixed with concentrated hydrochloric acid and ethyl acetate
15. 15
    その他the resulting organic layer was separated
16. 16
    洗浄washed with water
17. 17
    乾燥a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
18. 18
    その他By removing the solvent
19. 19
    workup.DISTILLATIONby distillation under a reduced pressure

実験手順

In a stream of argon, 60% sodium hydride was dissolved in 10 ml of tetrahydrofuran, and the solution was mixed with 2.0 g of benzyl cyanide, stirred for 1 hour at room temperature, further mixed with 3.69 g of 1,4-dibromobutane and again stirred for 16 hours at room temperature. The reaction mixture was mixed with water and ethyl acetate, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography, and the resulting hexane eluate was mixed with 45 ml of sulfuric acid and subjected to 24 hours of heating under reflux. After cooling down to room temperature, the reaction solution was mixed with ice water and ethyl acetate to separate water layer which was subsequently mixed with concentrated hydrochloric acid and ethyl acetate, and the resulting organic layer was separated, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. By removing the solvent by distillation under a reduced pressure, 978 mg of 1-phenylcyclopentanecarboxylic acid was obtained.

出典