Sodium Hydroxide → HCID 57435157, compound

Participants

Reaction Steps

Freshly prepared aq. NaOH (10 M in H2O, 1.22 mmol) was added to a stirring, room temperature solution of 5-(3-phenylpropyl)-1H-pyrrole-2-carboxylic acid ethyl ester (85) (0.0629 g, 0.244 mmol) in MeOH (0.61 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC. The product was concentrated and then 2 mL of diethyl ether and 2 mL of H2O were added. The organic layer was removed and discarded, then 2 mL of diethyl ether was added, and 10% aq. HCl was added dropwise until the pH=2. The diethyl ether later was removed, and the aqueous was extracted with another portion of diethyl ether. The combined organics were dried, and concentrated to provide the desired product. (Note: An undesired impurity has a retention time of 10.85 min by HPLC. HPLC: 9.91 min.

Provenance & Evidence