Reacción #62092

Ecuación de reacción

diisopropyl azodicarboxylate

Triphenylphosphine

methyl 2-chloro-3-[4-(2-hydroxyethyl)phenyl]propanoate

4-(benzyloxy)phenol

→

desired product

Rendimiento 67.1%

Methyl 3-(4-{2-[4-(benzyloxy)phenoxy]ethyl}phenyl)-2-chloropropanoate

Rendimiento 67.1%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool
2. 2
   Otrothe solvent was evaporated under reduced pressure
3. 3
   OtroThe crude product was purified by flash chromatography
4. 4
   workup.ADDITIONa 80:20 mixture of heptane and EtOAc as eluent

Procedimiento

Triphenylphosphine (2.4 g, 9 mmol) was added to a solution of methyl 2-chloro-3-[4-(2-hydroxyethyl)phenyl]propanoate (2.1 g, 8.5 mmol) and 4-(benzyloxy)phenol (1.7 g, 8 mmol) in 20 ml toluene under nitrogen atmosphere. The solution was warmed to 55° C. and diisopropyl azodicarboxylate (1.8 g, 9 mmol) was added. The reaction mixture was stirred at 55° C. overnight. The mixture was allowed to cool and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography using a 80:20 mixture of heptane and EtOAc as eluent to yield 2.28 g of the desired product (yield 61%) as colourless crystals.

Fuente