Sodium Chloride → 1-(4-Octylphenoxy)-3-(pyrrol-1-yl)propan-2-one

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Reaction Steps

1.24 g (12.1 mmol) acetic anhydride are mixed with 10 ml absolute DMSO, stirred at room temperature for 10 min and added drop-wise to a solution of 0.100 g (0.304 mmol) 1-(4-octylphenoxy)-3-(pyrrol-1-yl)propan-2-ol in 10 ml absolute DMSO. Having stirred for 19 hours, the solution is poured into a mixture of 5% sodium hydrogen carbonate solution and saturated NaCl solution (1:1, v/v) and hydrolyzed for 10 min. Four extractions with diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps using saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave a brownish oil which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 97:3) and yields the product as a white solid.

Provenance & Evidence