Reacción #65582

Ecuación de reacción

hexane

hexane ethyl acetate

1-oxaspiro[2.11]tetradecane

boron trifluoride etherate

→

clear oil

Rendimiento 34.0%

Cyclododecanecarboxaldehyde

Rendimiento 34.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)

Fuente