Ammonium Chloride → 5-Chloro-2-hex-1-enyl-1H-indole

HRID 2406655Notes

Reaction equation

HRID 2406655 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH3:6].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41]([CH:46]=O)=[CH:40]2.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Cl:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41]([CH:46]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:40]2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724565Pentyltriphenylphosphonium bromideHCID 2733832Lithium HexamethyldisilazideHCID 122033185-Chloro-1H-indole-2-carbaldehyde

Product 1

HCID 687508525-Chloro-2-hex-1-enyl-1H-indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To the cold suspension of Pentyl-triphenyl-phosphonium bromide in THF was added LiHMDS in THF and the mixture was stirred for 30 minutes. A solution of 5-Chloro-1H-indole-2-carbaldehyde in THF was added to the reaction mixture and stirred for 3 hours. The reaction mixture was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-336dc6c088b0420faa28c8c5551b84c1
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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