Potassium Hydroxide → 3,4-Diethylpyrrole

Participants

Reaction Conditions

Reaction Steps

Ethyl 3,4-diethylpyrrole-2-carboxylate obtained in Step (6) (2.056 g, 10.53 mmol), ethylene glycol (100 ml), and potassium hydroxide (3.5 g) were placed in a light-shielded reaction vessel equipped with a reflux condenser. Then, the inside of the reaction vessel was replaced with nitrogen and the mixture was stirred at 160° C. for 2.5 hours. After that, the reaction solution cooled to room temperature was poured into ice water, and extracted with ethyl acetate, and the extract was washed with an aqueous solution of sodium bicarbonate, water, and a saturated salt solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, thereby to obtain 3,4-diethylpyrrole. Again, 3,4-diethylpyrrole obtained by this reaction, benzyl-5-acetoxymethyl-4-n-butyl-3-methylpyrrole-2-carboxylate obtained in Step (3) (7.21 g, 21 mmol), acetic acid (10 ml), and ethanol (150 ml) were fed into a light-shielded reaction vessel equipped with a reflux condenser, and was refluxed for 18 hours. After the reflux, the resultant was cooled to room temperature, ethanol (50 ml) was added, and was left standing at 0° C. for 5 hours. The precipitated crystal was filtered out and thoroughly washed with ethanol to yield 2,5-bis(5-benzylcarbonyl-3-n-butyl-4-methyl-2-pyrroylmethyl)-3,4-dimethyl-1H-pyrrole (5.25 g, 72% yield).

Provenance & Evidence