Lithium Hexamethyldisilazide → 5-Chloro-2-(5-methyl-hex-1-enyl)-1H-indole

HRID 2406677

Reaction equation

HRID 2406677 reaction equation
[Br-].[CH3:2][CH:3]([CH3:26])[CH2:4][CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42]([CH:47]=O)=[CH:41]2>C1COCC1>[Cl:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42]([CH:47]=[CH:6][CH2:5][CH2:4][CH:3]([CH3:26])[CH3:2])=[CH:41]2

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 10928070Phosphonium, (4-methylpentyl)triphenyl-, bromideHCID 122033185-Chloro-1H-indole-2-carbaldehyde

Product 1

HCID 687513205-Chloro-2-(5-methyl-hex-1-enyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the cold suspension of (4-methyl-pentyl)-triphenyl-phosphonium bromide in THF was added LiHMDS in THF and the mixture was stirred for 30 minutes and then the solution of 5-chloro-1H-indole-2-carbaldehyde was added to the reaction mixture and stirred for 3 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The product, 5-chloro-2-(5-methyl-hex-1-enyl)-1H-indole was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. customThe product, 5-chloro-2-(5-methyl-hex-1-enyl)-1H-indole was purified by column chromatography

Sources & evidence

ORD record
ord-d2a9e4774b46443698e45265323b5eef
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Linked notes

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