Reaktion #46782

Reaktionsgleichung

NH4Cl

isopropenylmagnesium bromide

2-methoxynitrobenzene

→

expected compound

7-Methoxy-2-methyl-1H-indole

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture is left
2. 2
   Sonstigeto return to 0° C
3. 3
   Extraktionextracted with ether
4. 4
   Waschenthe organic phase is washed with a saturated NaCl solution
5. 5
   Trocknendried over MgSO4
6. 6
   Sonstigethe solvent is evaporated under vacuum
7. 7
   SonstigeThe residue is chromatographed on silica gel, elution

Vorschrift

800 ml of a 0.5M solution of isopropenylmagnesium bromide in THF is cooled to −40° C. under a nitrogen atmosphere, a solution of 20.4 g of 2-methoxynitrobenzene in 125 ml of THF is then added dropwise and the mixture is left stirring for 1 hour while allowing the temperature to return to 0° C. The reaction mixture is poured into a saturated NH4Cl solution and extracted with ether, the organic phase is washed with a saturated NaCl solution and dried over MgSO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with cyclohexane and then with a cyclohexane/EtOAc mixture (90/10; v/v). 2.45 g of the expected compound are obtained in the form of an oil.

Quelle