Ethyl 4-iso-butylbenzoylformate → 4-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanone

Participants

Reaction Steps

A total of 3.5 mL (10.5 mmol) of 3.0 M 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 500 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.

Provenance & Evidence