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ChemicalBook CAS DataBase List 5-Methoxyindole
1006-94-6

5-Methoxyindole synthesis

14synthesis methods
The synthesis of 5-methoxyindole from 5-methoxy-2-oxindole: Conversion of 5-methoxy-2-oxindole to 5-methoxyindole was accomplishedby the chlorination of 5-methoxy-2-oxindole with triphenylphosphine-carbontetrachloride in acetonitrile followed by the catalytic reduction of a chlorine atom in 66% total yield.
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Yield:1006-94-6 99%

Reaction Conditions:

with water;1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran; for 18 h;Reflux;

Steps:

4.3. General procedures for the deprotection of N-pivaloylindoles

General procedure: Method C: DBU (4 equiv) and water (2 equiv) was added to a solution of 1-pivaloyl derivatives (1 equiv) in THF (3 mL×mmol) and was stirred to reflux until the disappearance of the starting indole. The reaction mixture was eluyed with EtOAc (10 mL) and was washed with a saturated aqueous NH4Cl solution (4 mL×mmol). The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were dried over Na2SO4 and evaporated to afford the corresponding unprotected compound.

References:

Ruiz, Míriam;Sánchez, J. Domingo;López-Alvarado, Pilar;Menéndez, J. Carlos [Tetrahedron,2012,vol. 68,# 2,p. 705 - 710] Location in patent:experimental part

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