Reaktion #65985

Reaktionsgleichung

hexyl iodide

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

sodium methoxide

→

white crystals

Ausbeute 62.0%

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

Ausbeute 62.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle