Réaction #65985

Équation de réaction

hexyl iodide

5-hydroxy-2-methyl-1H-indole-3-acetic acid

sodium methoxide

→

white crystals

Rendement 62.0%

5-(Hexyloxy)-2-methyl-1H-indole-3-acetic acid

Rendement 62.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   AutreThe solution is evaporated
2. 2
   workup.ADDITIONdimethylformamide (40 mL) is added
3. 3
   AutreAfter 2 days the solvent is removed
4. 4
   Autrethe residue is partitioned between ethyl acetate and pH=4 buffer
5. 5
   AutreThe organic layer is separated
6. 6
   Séchagedried over MgSO4
7. 7
   Autreevaporated to 8.6 g of a brown solid
8. 8
   AutreRecrystallization from ethanol/water

Mode opératoire

To a solution of 5-hydroxy-2-methyl-1H-indole-3-acetic acid (7.17 g, 35.0 mmol) in methanol (40 mL) is added sodium methoxide (70 mmol). The solution is evaporated, dimethylformamide (40 mL) is added followed by hexyl iodide (35.0 mmol). After 2 days the solvent is removed and the residue is partitioned between ethyl acetate and pH=4 buffer. The organic layer is separated, dried over MgSO4 and evaporated to 8.6 g of a brown solid. Recrystallization from ethanol/water affords 6.23 g (62%) of white crystals, m.p. 65°-67° C.

Source