Reacción #2254223

Ecuación de reacción

potassium hydroxide

Ethylene glycol

methyl 2-cyano-2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetate

→

2-[9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile

Rendimiento 82.6%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONthe resulting mix
2. 2
   workup.ADDITIONthe reaction mix
3. 3
   Temperaturawas cooled
4. 4
   Extracciónthe product was extracted by Et2O (3×400 ml)
5. 5
   Lavadowashed with water (200 ml)
6. 6
   Secadodried (Na2SO4)
7. 7
   Concentraciónconcentrated
8. 8
   Otrothe residual was purified by flash chromatography (340 g silica gel column
9. 9
   Lavadoeluted by EtOAc in hexane

Procedimiento

Ethylene glycol (300 ml) was added to methyl 2-cyano-2-[9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetate (15.43 g, 49 mmol) followed by potassium hydroxide (5.5 g, 98 mmol), the resulting mix was heated to 120° C., after 3 h, the reaction mix was cooled and water (300 ml) was added, the product was extracted by Et2O (3×400 ml), washed with water (200 ml), dried (Na2SO4) and concentrated, the residual was purified by flash chromatography (340 g silica gel column, eluted by EtOAc in hexane: 3% 2 CV; 3-25%, 12 CV; 25-40% 6 CV to give 2-[9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (10.37 g, 82% yield, m/z 257.0 [M+H]+ observed).

Fuente