Water → 5-Dimethoxymethyl-1-(4-methylphenyl)sulfonylindole-2-carboxaldehyde

HRID 1281158Notes

Reaction equation

HRID 1281158 reaction equation
[CH3:1][O:2][CH:3]([O:23][CH3:24])[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:8]=[CH:7]2.C([Li])CCC.CN(C)[CH:32]=[O:33].O>O1CCCC1>[CH3:1][O:2][CH:3]([O:23][CH3:24])[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:8]([CH:32]=[O:33])=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 184268655-Dimethoxymethyl-1-(4-methylphenyl)sulfonylindoleHCID 178418339Butyllithium

Product 1

HCID 184268135-Dimethoxymethyl-1-(4-methylphenyl)sulfonylindole-2-carboxaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-dimethoxymethyl-1-(4-methylphenyl)sulfonylindole (2.37 g, 6.87 mmol) in tetrahydrofuran (35 mL) was added n-butyllithium (1.6 mol/L in hexanes; 6.2 mL, 9.9 mmol) at −78° C. under nitrogen atmosphere, and the mixture was stirred for 2 h. Then dimethylformamide (1.1 mL, 14 mmol) was added, and the mixture was stirred for 20 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (4:1 hexane/ethyl acetate) followed by trituration with hexane to afford 5-dimethoxymethyl-1-(4-methylphenyl)sulfonylindole-2-carboxaldehyde (1.89 g, 74%).

Workup

  1. stirringthe mixture was stirred for 20 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography (4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-696ec87d01e543d8a0aa9a67b0750dbd
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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