Iodoethane → Indole

HRID 987162Notes

Reaction equation

HRID 987162 reaction equation
C(OC([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].CC(C1C=C(C(C)(C)CC)C=CC=1OCC(O)=O)(C)CC.[I-].C(Br)C1C=CC=CC=1.C(I)C.[H-].[Na+].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>[O-2].[O-2].[Mn+4].CN(C=O)C.C1COCC1>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:6]1

Participants

13

Reactant 9

HCID 6340IodoethaneHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 30165Iodide IonHCID 73125Ethyl indole-2-carboxylateHCID 83411(2,4-Bis(1,1-dimethylpropyl)phenoxy)acetic acidHCID 166653HydrideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 21226445Aluminium lithium hydride

Product 1

HCID 798Indole

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Aldehyde IX is prepared from Indol-2-carboxylic acid ethyl ester I in two steps: (1) Reduction with lithium aluminium hydride or other hydride in a suitable solvent such as THF at 0° C. and (2) oxidation with an oxidizing reagent such as manganese dioxide in a solvent such as THF. Aldehyde IX can be alkylated by a suitable alkyl bromide (or iodide), such as benzyl bromide or ethyl iodide in the presence of a strong base such as sodium hydride or KHMDS in a solvent such as DMF to yield indole X. Indole X can be converted to an unsaturated acid XI in two steps: (1) Wittig reaction with a suitable reagent such as trimethyl phosphonoacetate in the presence of a base such as sodium hydride in a solvent such as THF and (2) Hydrolysis by aqueous sodium hydroxide.

Workup

  1. customat 0° C.

Sources & evidence

ORD record
ord-1ba50e4089b049edb24d60b5da4e322e
Source dataset
uspto-grants-2003_10
Patent number
US06630496B1

Reaction notes

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