Reaction #65985

Reaction equation

hexyl iodide

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

sodium methoxide

→

white crystals

Yield 62.0%

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

Yield 62.0%

Solvents

methanol

Conditions

Workup

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

Procedure

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