Diethyl Ether → 1-[3-(Biphenyl-4-yloxy)-2-hydroxypropyl]indole-5-carbonitrile

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Reaction Steps

0.34 g (2.02 mmol) 4-phenyl phenol are dissolved in 5 ml absolute THF under nitrogen and mixed drop-wise with 0.1 ml (1.0 mmol) tert-butyllithium with constant stirring. The mixture is stirred at room temperature for 5 min. Thereafter, the solution of 0.20 g (1.0 mmol) 1-oxiranylmethylindole-5-carbonitrile (Example 26A) in 5 ml absolute THF is added drop-wise. The batch is heated at 100° C. for 4 hours. Having cooled down, the batch is mixed with 100 ml diethyl ether and extracted three times using water. The aqueous phase is extracted twice using ethyl acetate and the combined organic phases are dried on sodium sulfate, filtrated and the solvent is removed in vacuo. The residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 7:3). The product is obtained as a solid.

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