反応 #65985

反応方程式

hexyl iodide

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

sodium methoxide

→

white crystals

収率 62.0%

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

収率 62.0%

溶媒

methanol

反応条件

後処理

1. 1
   その他The solution is evaporated
2. 2
   workup.ADDITIONdimethylformamide (40 mL) is added
3. 3
   その他After 2 days the solvent is removed
4. 4
   その他the residue is partitioned between ethyl acetate and pH=4 buffer
5. 5
   その他The organic layer is separated
6. 6
   乾燥dried over MgSO4
7. 7
   その他evaporated to 8.6 g of a brown solid
8. 8
   その他Recrystallization from ethanol/water

実験手順

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.

出典