Sodium Iodide → 4-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]benzaldehyde

HRID 2110851Notes

Reaction equation

HRID 2110851 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:23]=[O:24].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:29]([O:28][C:27]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=1[CH2:19][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:30]([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 136982-PhenylindoleHCID 24758Sodium hydrideHCID 231573903-(Chloromethyl)-4-isobutoxybenzaldehyde

Product 1

HCID 231599294-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]benzaldehydeYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-phenyl-1H-indole (0.94 g, 4.85 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% in oil, 0.19 g, 4.85 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 5 min. 3-(Chloromethyl)-4-isobutoxybenzaldehyde (1.0 g, 4.41 mmol) and sodium iodide (0.73 g, 4.85 mmol) were added to the obtained mixture and the mixture was stirred at the same temperature for 2 hr. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, and the mixture was washed with 5% aqueous potassium hydrogensulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (0.60 g, yield 36%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 5 min
  2. stirringthe mixture was stirred at the same temperature for 2 hr
  3. customAfter completion of the reaction
  4. washthe mixture was washed with 5% aqueous potassium hydrogensulfate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-dad632bfc0054ae8a1a7ea8bed207ad3
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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