Citric Acid → 1,3-Bis(4-methoxyphenyl)-2-phenylpropane-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-methoxyphenyl)-2-phenylethan-1-one (1.0 equiv.) in THF at −78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]NLi. The solution was stirred for 1 h at −78° C., followed by addition of 1.2 equiv. of p-anisoyl chloride. The reaction mixture was stirred for 10 min at −78° C. and then for 22 h at rt, acidified with 10% citric acid, and extracted with EtOAc. The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent in vacuo provided a crude solid which was purified by flash chromatography (CH2Cl2) to give 1,3-bis(4-methoxyphenyl)-2-phenylpropane-1,3-dione.

Provenance & Evidence