반응 #353280

반응 방정식

1-(2-phenylethyl)-4-piperidinecarboxaldehyde

n-butyllithium

3-bromobenzo[b]thiophene

→

title compound

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

용매

ethyl ether

ethyl ether

hexane

ethyl ether

반응 조건

후처리

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
   기타remove the ice bath
5. 5
   workup.STIRRINGstir for an additional 1 hour
6. 6
   기타Quench with saturated ammonium chloride (150 mL)
7. 7
   workup.STIRRINGstir overnight
8. 8
   기타Separate the organic phase
9. 9
   추출extract the aqueous phase with ethyl ether and methylene chloride
10. 10
    건조dry (MgSO4)
11. 11
    기타evaporate the solvent in vacuo
12. 12
    기타Purify by recrystallization (isopropanol)

실험 절차

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.

출처