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

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Reaction Steps

0.048 g (1.200 mmol) sodium hydride as 60% dispersion in mineral oil is suspended in 10 ml absolute DMF, stirred at room temperature for 10 min and admixed with 0.077 g (1.15 mmol) pyrrole. Having stirred for one hour, a solution of 0.300 g (1.14 mmol) 2-(4-octylphenoxymethyl)oxirane (Kuliev et al. Uch. Zap. Azerb. Gos. Univ. Ser. Khim Nauk. 1964, 4, 97; Chem. Abstr. 1966, 65, 640c) in 10 ml absolute DMF is added drop-wise. The mixture is stirred for 19 hours, hydrolyzed with a semi-saturated NaCl solution and extracted four times using diethyl ether. The combined organic phases are concentrated to half the volume on the rotary evaporator and washed three times with saturated NaCl solution. Drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a red oil which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 95:5) and yields the product as a yellowish oil.

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