Sodium Hydroxide → HCID 20469139, compound

Participants

Reaction Steps

Ethyl-1,4-dimethyl-3-ethoxycarbonyl-5-(1-methylpyrrol-2-oyl)pyrrole-2-acetate (7 g) is dissolved in 20 ml of ethanol, aqueous 50% sodium hydroxide solution (50 ml) is added, and the resulting solution is heated at reflux for about one hour. It is cooled to room temperature, and acidified to yield a white precipitate which in turn is filtered and dried to afford 5.2 g of 1,4-dimethyl-3-hydroxycarbonyl-5-(1-methylpyrrol-2-oyl)pyrrole-2-acetic acid (a diacid). The diacid is partially esterified by treatment with 200 ml of ethanol containing 1.0 g of Bio-Rad® 50W×8 H+ resin at reflux for two hours. After filtration and removal of the excess ethanol, the crude product is purified by HPLC to yield 3.8 g (55%) of white crystalline ethyl 1,4-dimethyl-3-hydroxycarbonyl-5-(1-methylpyrrol-2-oyl)pyrrole-2-acetate.

Provenance & Evidence