反応 #353280

反応方程式

1-(2-phenylethyl)-4-piperidinecarboxaldehyde

n-butyllithium

3-bromobenzo[b]thiophene

→

title compound

α-[1-(2-Phenylethyl)-4-piperidinyl]-3-benzo[b]thiophenemethanol

溶媒

ethyl ether

ethyl ether

hexane

ethyl ether

反応条件

後処理

1. 1
   workup.ADDITIONAdd, by dropwise addition
2. 2
   workup.ADDITIONthen add, by dropwise addition
3. 3
   workup.STIRRINGStir for 5 hours at -78° C.
4. 4
   その他remove the ice bath
5. 5
   workup.STIRRINGstir for an additional 1 hour
6. 6
   その他Quench with saturated ammonium chloride (150 mL)
7. 7
   workup.STIRRINGstir overnight
8. 8
   その他Separate the organic phase
9. 9
   抽出extract the aqueous phase with ethyl ether and methylene chloride
10. 10
    乾燥dry (MgSO4)
11. 11
    その他evaporate the solvent in vacuo
12. 12
    その他Purify by recrystallization (isopropanol)

実験手順

Dissolve n-butyllithium (9.4 mL of a 2.5M solution in hexane, 23.46 mmol) in anhydrous ethyl ether (100 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, a solution of 3-bromobenzo[b]thiophene (5.0 g, 23.46 mmol) in anhydrous ethyl ether (50 mL). Stir at -78° C. for 30 minutes then add, by dropwise addition, a solution of 1-(2-phenylethyl)-4-piperidinecarboxaldehyde (5.10 g, 23.46 mmol) in anhydrous ethyl ether (50 mL). Stir for 5 hours at -78° C., remove the ice bath and stir for an additional 1 hour. Quench with saturated ammonium chloride (150 mL) and stir overnight. Separate the organic phase and extract the aqueous phase with ethyl ether and methylene chloride. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by recrystallization (isopropanol) to give the title compound as an off-white solid.

出典