Reaktion #409205

Reaktionsgleichung

NaH

3-phenoxybenzylalcohol

NaH

ethyl(E)-3-(2-(bromomethyl)phenyl)-2-propenoate

→

desired material

Ethyl(E)-3-(2-((3-phenoxy)benzyloxy)phenyl)-2-propenoate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen quenched
2. 2
   workup.ADDITIONThe mixture was diluted with Et2O (25 ml)
3. 3
   Waschenwashed with water (3×20 ml) and brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated

Vorschrift

To a solution of 3-phenoxybenzylalcohol (545 mg; 2.72 mmol) in DMF (5 ml) was added NaH (92 mg; 3.1 mmol; 80% dispersion in oil) and ethyl(E)-3-(2-(bromomethyl)phenyl)-2-propenoate (810 mg; 3.0 mmol). After 6 h at r.t., 20 mg extra NaH was added. The final mixture was stirred at r.t. for 10 h then quenched using 0.3 ml of AcOH. The mixture was diluted with Et2O (25 ml), washed with water (3×20 ml) and brine, dried over MgSO4 and concentrated. Flash chromatography with EtOAc:toluene 5:95 afforded the desired material.

Quelle