Butanal, 4-[(tetrahydro-2H-pyran-2-yl)oxy]- → 2-{[5-(4-Chlorophenyl)pent-4-en-1-yl]oxy}oxane

Beteiligte Stoffe

Reaktionsschritte

In an argon atmosphere, butyllithium (10%; 37 ml) was added dropwise to a suspension of (4-chlorobenzyl)triphenylphosphonium chloride (24 g) in tetrahydrofuran (70 ml) with ice-cooling and stirring. After stirring at the same temperature for 30 minutes, a solution of 4-tetrahydropyranyloxy-1-butanal (9 g) in tetrahydrofuran (30 ml) was added dropwise, and the mixture was stirred at room temperature for 2 hours. The tetrahydrofuran was distilled off under reduced pressure and water was added to the residue, followed by extraction with petroleum ether. After washing with water and drying over magnesium sulfate, the solvent was distilled off, and the residue was subjected to silica gel column chromatography, elution being carried out with chloroform to give 1-(4-chlorophenyl)-5-(2-tetrahydropyranyloxy)-1-pentene (7 g) as a light-yellow oil.

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