Reaktion #1183013

Reaktionsgleichung

1,4-dioxane

1,4-Dioxa-8-azaspiro[4,5]decane

1-(benzyloxy)-4-iodobenzene

sodium tert-butoxide

→

compound

Ausbeute 73.6%

8-[4-(benzyloxy)phenyl]-1,4-dioxa-8-azaspiro[4,5]decane

Ausbeute 73.6%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was cooled with ice
2. 2
   Waschenwashed with water and saturated saline in that order
3. 3
   Trocknenthe organic layer was dried with sodium sulfate
4. 4
   SonstigeThe solvent was evaporated off under reduced pressure
5. 5
   Sonstigethe resulting residue was purified through silica gel column chromatography (eluate: chloroform/ethyl acetate=10/1)
6. 6
   Filtrationfiltered under suction

Vorschrift

1,4-Dioxa-8-azaspiro[4,5]decane (653 g, 4.56 mol), 1-(benzyloxy)-4-iodobenzene (1 kg, 3.8 mol), sodium tert-butoxide (511 g, 5.32 mol), Pd(OAc)2 (17 g, 76 mmol) and biphenyl-2-yl(dicyclohexyl) phosphine (54 g, 152 mmol) were mixed, and 1,4-dioxane, this was stirred overnight at 80° C. in a nitrogen atmosphere. The reaction solution was cooled with ice, diluted with ethyl acetate, washed with water and saturated saline in that order, and the organic layer was dried with sodium sulfate. The solvent was evaporated off under reduced pressure, and the resulting residue was purified through silica gel column chromatography (eluate: chloroform/ethyl acetate=10/1), and the resulting crude product was suspended in a mixed solvent of chloroform/hexane and filtered under suction to obtain the entitled compound (910 g, 73%) as a brown solid.

Quelle