Reaktion #93899

Reaktionsgleichung

2-oxocycloheptaneacetonitrile

methyl iodide

sodium tert-amylate

toluene

→

1-methyl-2-oxocycloheptaneacetonitrile

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto stand overnight at room temperature
2. 2
   WaschenThe mixture is washed with 1% aqueous HCl, cold water
3. 3
   Trocknenbrine, dried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give an oily residue
6. 6
   workup.DISTILLATIONDistillation under reduced pressure

Vorschrift

To a stirred solution of 2-oxocycloheptaneacetonitrile (44.6 g, 0.297 mole), and methyl iodide (42.6 g, 0.3 mole) in dry benzene (200 ml) under nitrogen, is added dropwise a solution of sodium tert-amylate in toluene (340 ml, 0.297 mole). The reaction is exothermic and a bright yellow colour appears. The mixture is stirred at 65° C. for 4 hr., then allowed to stand overnight at room temperature. The mixture is washed with 1% aqueous HCl, cold water, then brine, dried (MgSO4) and concentrated to give an oily residue. Distillation under reduced pressure gives 1-methyl-2-oxocycloheptaneacetonitrile (13, R1 = CH3, R2 = H and m = 4), bp 152°-158° C./14 mm.

Quelle