Reaktion #518034

Reaktionsgleichung

PPTS

n-BuLi

2-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolane

4-benzyloxy-benzonitrile

→

3-[2-(4-Benzyloxy-benzoyl)-5-methoxy-phenyl]-1-phenyl-propan-1-one

Lösungsmittel

acetone

H2O

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   Temperaturrefluxed overnight
3. 3
   SonstigeThe solution was then quenched with sat. NH4Cl
4. 4
   Sonstigethe solvent was evaporated
5. 5
   Temperaturwas refluxed overnight
6. 6
   SonstigeRegular workup and column purification

Vorschrift

A solution of 2-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolane (0.9 g, 2.5 mmol) in 10 ml of dry THF was cooled to −78° C. and n-BuLi (2.5 M in hexane, 1 ml) was added dropwise. The solution was stirred at −78° C. for 2 h and 4-benzyloxy-benzonitrile (0.575 g, 2.75 mmol) in 2 ml of THF was added. The mixture was allowed to warm to room temperature and refluxed overnight. The solution was then quenched with sat. NH4Cl and the solvent was evaporated. A solution of the residue in 20 ml of wet acetone, 5 ml of H2O containing PPTS (188 mg, 0.75 mmol) was refluxed overnight. Regular workup and column purification afforded an unoptimized weight of 0.8 g 3-[2-(4-Benzyloxy-benzoyl)-5-methoxy-phenyl]-1-phenyl-propan-1-one.

Quelle