반응 #65985

반응 방정식

hexyl iodide

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

sodium methoxide

→

white crystals

수율 62.0%

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

수율 62.0%

용매

methanol

반응 조건

후처리

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

실험 절차

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.

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