Réaction #7970

Équation de réaction

NH4Cl

5-methoxy-1H-indene

MeLi

iodopropane

→

5-methoxy-1-propyl-1H-indene

Rendement 108.3%

Solvants

Et2O

Et2O

Et2O

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONadded dropwise over 10 minutes
2. 2
   Températurecooled in an ice bath
3. 3
   workup.STIRRINGThe mixture was stirred at ice bath temperature
4. 4
   Températurewith gradual warming to room temperature
5. 5
   workup.STIRRINGAfter stirring at room temperature overnight
6. 6
   workup.STIRRINGshaken
7. 7
   LavageThe organic phase was washed with brine
8. 8
   Séchagedried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Autreevaporated under vacuum

Mode opératoire

A solution of 5-methoxy-1H-indene (0.895 g, 6.12 mmol) in anhydrous Et2O (7.5 mL) was treated with 1.4M MeLi in Et2O (4.7 mL, 6.58 mmol) added dropwise over 10 minutes. The resulting hazy solution was stirred at room temperature an additional 15 minutes, then cooled in an ice bath and treated with iodopropane (1.00 mL, 10.3 mmol). The mixture was stirred at ice bath temperature with gradual warming to room temperature. After stirring at room temperature overnight, the mixture was treated with saturated aq. NH4Cl (10 mL) and Et2O (15 mL) and shaken. The organic phase was washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to afford a mixture (1.248 g) of 5-methoxy-1-propyl-1H-indene and 6-methoxy-1-propyl-1H-indene as an oil.

Source