Reaktion #456335

Reaktionsgleichung

phenylmagnesium bromide

ethyl 4-isobutylbenzoylformate

3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

→

4-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanone

Ausbeute 29.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto provide an oil, which
2. 2
   Sonstigewas purified over 400 g of SiO2
3. 3
   Waschenby eluting with 5000 mL of CHCl3, 500 mL of EtOH/CHCl3 (3/97) and 500 mL of EtOH/CHCl3 (8/92)

Vorschrift

A total of 3.5 mL (10.5 mmol) of 3.0M phenylmagnesium bromide was added to a solution of 2.3 g (10 mmol) of ethyl 4-isobutylbenzoylformate in THF in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to provide an oil, which was purified over 400 g of SiO2 by eluting with 5000 mL of CHCl3, 500 mL of EtOH/CHCl3 (3/97) and 500 mL of EtOH/CHCl3 (8/92) to provide 1.2 g (29% yield) of 4-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanone as a tan powder recrystallized from CHCl3 and hexanes.

Quelle