Diethyl Ether → HCID 178467905, compound

Participants

Reaction Steps

To a suspension of 2.86 g (7 mM) of the phosphonium salt, prepared as indicated above in a finely divided powder form, in 20 ml of anhydrous ether, 5 ml (7 mM) of a 1.6 N solution of butyllithium in hexane were added under argon atmosphere. To the thus obtained red solution, 0.855 ml (7 mM) of hexanal, previously distilled, were added dropwise and the mixture was kept at reflux temperature during 1 h, whereupon it was poured into water. After extracted with pentane, washing with water of the separated organic phases, drying and evaporation there was obtained a residue which by fractional distillation in a bulb distillation apparatus gave 0.8556 (81 %) of a 33:66 mixture of undeca-1,3trans,5cis-triene and undeca-1,3trans,5trans-triene. The analysis was conducted by vapour phase chromatography on a column of the type: Sp 1000, 4 mm × 2.5 m; 155°.

Provenance & Evidence