Reacción #65985

Ecuación de reacción

hexyl iodide

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

sodium methoxide

→

white crystals

Rendimiento 62.0%

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

Rendimiento 62.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente