Reaktion #215979

Reaktionsgleichung

(3-phenylpropyl)triphenylphosphonium bromide

methyl 4-formylbenzoate

→

methyl (E)-4-(4-phenyl-1-butenyl)benzoate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigecondensed

Vorschrift

Using the conditions in example 1(A), (3-phenylpropyl)triphenylphosphonium bromide and methyl 4-formylbenzoate are condensed, providing methyl (E)-4-(4-phenyl-1-butenyl)benzoate as a colorless oil after chromatographic separation from the later-eluting (Z) isomer. This is reduced with lithium aluminum hydride in THF in the usual fashion to provide (E)-4-(4-phenyl-1-butenyl)phenylmethanol as a colorless oil. Oxidation with pyridinium dichromate in the usual fashion provides (E)-4-(4-phenyl-1-butenyl)benzaldehyde as a colorless oil after chromatography.

Quelle