تفاعل #65985

معادلة التفاعل

hexyl iodide

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

sodium methoxide

→

white crystals

المردود 62.0%

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

المردود 62.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر