Water → 4-[4-(4-Ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzene

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Reaction Steps

0.01 mol of a solution of butyllithium in hexane is added at -30° C. with stirring to 1.9 g (0.01 mol) of 3-[p-ethoxyphenyl]-3-methyl-1-butine in 10 ml of absolute tetrahydrofuran. After stirring for 3 hours, a solution of 2.2 g (0.01 mol) of 4-fluoro-3-phenoxy-benzaldehyde in 10 ml of tetrahydrofuran is added to the reaction mixture. The reaction mixture is warmed to room temperature and, after stirring at this temperature for 5 hours, water and dichloromethane (100 ml each) are added. The organic phase is separated off and concentrated in vacuo. 3.6 g of crude product are obtained, which contains 85% of 1-[4-fluoro-3-phenoxy-phenyl]-4-[p-ethoxyphenyl]-4-methyl-pent-1-in-1-ol (in addition to 7% of the corresponding ketone) according to GC-MS analysis. The crude product is catalytically hydrogenated under the conditions described in Example 8 δ). 3 g of 1-[4-fluoro-3-phenoxy-phenyl]-4-[p-ethoxyphenyl]-4-methyl-pentane (89% pure according to GC-MS analysis=2.7 g=69% of theory) are obtained. The compound is obtained pure by chromatography on silica gel (nD20 : 1.5580).

Provenance & Evidence