Reaktion #65582

Reaktionsgleichung

hexane

hexane ethyl acetate

1-oxaspiro[2.11]tetradecane

boron trifluoride etherate

→

clear oil

Ausbeute 34.0%

Cyclododecanecarboxaldehyde

Ausbeute 34.0%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0° C.
2. 2
   SonstigeThe ice bath is removed and after 15 minutes at room temperature the solution
3. 3
   Sonstigeis partitioned between ether and saturated sodium bicarbonate
4. 4
   SonstigeThe organic phase is evaporated
5. 5
   Sonstigeto give a clear oil

Vorschrift

To 5.0 g (25.5 mmol) of 1-oxaspiro[2.11]tetradecane in 50 ml of dry ether at 0° C. is slowly added 1.8 ml (2.1 g, 14.6 mmol) of boron trifluoride etherate. The ice bath is removed and after 15 minutes at room temperature the solution is partitioned between ether and saturated sodium bicarbonate. The organic phase is evaporated to give a clear oil. Flash chromatography over silica gel using a hexane to hexane:ethyl acetate (9:1) gradient give 1.6 g (34%) of a clear oil: NMR (CDCl3) δ 1.28-1.8 (m, 18H), 2.03 (s, 1H), 2.42 (m, 1H), 9.62 (s, 1H)

Quelle