HCID 14500589, compound → HCID 21241942, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 4 g (100 mmol) of lithium aluminum hydride in 300 ml of anhydrous tetrahydrofuran was added dropwise, at room temperature, a solution of 18 g (100 mmol) of 1-butyl-2-propionylpyrrole in 100 ml of anhydrous tetrahydrofuran. The reaction mixture was refluxed for 30 minutes, cooled to 0° C. and the excess reagent destroyed by carefully adding ethyl acetate, saturated sodium sulfate solution and solid anhydrous sodium sulfate. The insoluble material was separated by filtration and the filtrate evaporated in vacuo. The unstable 1-butyl-2-(α-hydroxypropyl)pyrrole thus obtained (20 g, 110 mmol) was dissolved in 250 ml of methanol, the solution cooled to 0° C. and treated with 60 ml of glacial acetic acid and 14 g (220 mmol) of sodium cyanoborohydride. The reaction mixture was stirred at 0° C. for 30 minutes and thereafter for 75 minutes further at room temperature. It was then poured into 1000 ml of saturated sodium carbonate solution and the product extracted with ethyl acetate (3×500 ml). The combined extracts were washed with water (3×250 ml), dried and evaporated under reduced pressure. The residue was purified by column chromatography on 500 g of silica gel, using hexane-methylene chloride (95:5) as eluant, thus obtaining 8.7 g (52%) of the title compound, 1-butyl-2-propylpyrrole, as an oil.

Provenance & Evidence