Diisobutylaluminum hydride → 4-Ethoxy-1H-indole-6-carbaldehyde

HRID 502411Notes

Reaction equation

HRID 502411 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12]([C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[CH:19][NH:20]2)=[C:16]([O:23][CH2:24][CH3:25])[CH:15]=1)=O>O=[Mn]=O>[CH2:24]([O:23][C:16]1[CH:15]=[C:14]([CH:12]=[O:11])[CH:22]=[C:21]2[C:17]=1[CH:18]=[CH:19][NH:20]2)[CH3:25]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 45094531HCID 45094531, compound

Product 1

HCID 227429104-Ethoxy-1H-indole-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

The necessary intermediate 4-Ethoxy-1H-indole-6-carbaldehyde was synthesized following the procedure described in J. Org. Chem. 2004, 69, 6945 and ensuing DIBAL-H—reduction and MnO2—oxidation of the resultant 4-ethoxy-1H-indole-6-carboxylic acid methyl ester, as yellow solid.

Sources & evidence

ORD record
ord-90049a40fafa446bbe0f7a81c17ed027
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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