Reaktion #336458

Reaktionsgleichung

diethyl azodicarboxylate

6-diethylamino-1-hexanol

4-hydroxy-benzaldehyde

triphenylphosphine

→

4-[[6-(diethylamino)hexyl]oxy]benzaldehyde

Ausbeute 64.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the dropwise addition the mixture
2. 2
   SonstigeThe reaction mixture was then evaporated in a rotary evaporator
3. 3
   SonstigeThe residue was chromatographed on 400 g of neutral aluminium oxide (activity grade III) with hexane:ethyl acetate (7:3)

Vorschrift

A mixture of 2.17 g of 6-diethylamino-1-hexanol (J. Chem. Soc. 1942, 428), 1.52 g of 4-hydroxy-benzaldehyde and 3.3 g of triphenylphosphine in 100 ml of tetrahydrofuran was treated slowly at 20° with a solution of 1.97 g of diethyl azodicarboxylate. After the dropwise addition the mixture was stirred at room temperature for a further 5 hours. The reaction mixture was then evaporated in a rotary evaporator. The residue was chromatographed on 400 g of neutral aluminium oxide (activity grade III) with hexane:ethyl acetate (7:3). There were obtained 2.22 g (64%) of 4-[[6-(diethylamino)hexyl]oxy]benzaldehyde as a yellowish oil.

Quelle