HCID 23003163, compound → HCID 23003162, compound

HRID 396206Notes

Reaction equation

HRID 396206 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH:10]=[C:9]2[CH:20]=[O:21].[CH2:27]([Mg]Br)[CH3:28]>C1COCC1>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH:10]=[C:9]2[C:20](=[O:21])[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 23003163HCID 23003163, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 23003162HCID 23003162, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a flame dried flask was added a solution of 4-[5-(2,6-dichlorobenzyloxy)-3-formyl-indol-1-yl]butyronitrile (0.23 g, 0.59 mmol) in THF (10 mL) and cooled to −78° C. To this solution ethyl magnesium bromide (1.0M in THF, 0.65 mL, 0.65 mmol) was added via dropwise addition. The reaction was stirred at −78° C. for 3 h then warmed to room temperature slowly. After stirring at room temperature for 18 h, the reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over Na2SO4. Purification by flash column chromatography (silica gel, ethyl acetate/hexane) afforded three products, one of which was identified by NMR, IR and LC-MS as the ketone 4-[5-( 2,6-dichlorobenzyloxy)-3-propionyl-indol-1-yl]butyronitrile (0.034 g, 14%). MS(ES) m/e 415.0 [M+H]+. None of the expected secondary alcohol was recovered.

Workup

  1. customTo a flame dried flask
  2. temperaturethen warmed to room temperature slowly
  3. stirringAfter stirring at room temperature for 18 h
  4. customthe reaction was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customPurification by flash column chromatography (silica gel, ethyl acetate/hexane)
  8. customafforded three products, one of which
  9. customNone of the expected secondary alcohol was recovered

Sources & evidence

ORD record
ord-100b096f31d0488cbd15a94e7a6ad52a
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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