Sodium Hydroxide → 5-(p-Chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid

Participants

Reaction Steps

Crude ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate (505 mg) is suspended in 1 ml ethanol and heated to reflux. After all the solids dissolve, 5 ml of 2.5 N aqueous sodium hydroxide is added dropwise, causing an oil to separate at the end of the addition. However, the reaction mixture becomes homogeneous again after stirring vigorously at 100° for about 5 min. The reaction is then cooled, diluted with 5 ml water and acidified with 5.5 ml 2.5 N hydrochloric acid. The resulting precipitate is filtered, dried in vacuo to afford 478 mg of crude 5-(p-chlorobenzoyl)-3-hydroxycarbonyl-4-methoxy-1-methylpyrrole-2-acetic acid.

Provenance & Evidence