Ammonium Chloride → 2-oct-1-enyl-1H-indole

HRID 2406649Notes

Reaction equation

HRID 2406649 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[C:39]1[CH:47]=O.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH:47]([C:39]1[NH:38][C:46]2[C:41]([CH:40]=1)=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 96389Indole-2-carboxaldehydeHCID 2724567Heptyltriphenylphosphonium bromideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 687493232-oct-1-enyl-1H-indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of heptyl-triphenyl-phosphonium bromide in THF was added LiHMDS in THF and the mixture was stirred for 30 minutes and then the solution of 1H-indole-2-carbaldehyde 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-1cf0d7d9d35f4510ba0a0cb5d8df5b2d
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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