Sodium hydride → 5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 1012410Notes

Reaction equation

HRID 1012410 reaction equation
[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([CH:12]=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:33]=1>O1CCCC1.C(OCC)(=O)C>[C:1]1([C:7]2[N:11]([S:38]([C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)(=[O:40])=[O:39])[CH:10]=[C:9]([CH:12]=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 110520905-Phenyl-1H-pyrrole-3-carboxaldehydeHCID 12571517Pyridine-3-sulfonyl chloride hydrochloride

Product 1

HCID 862328815-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehydeYield 75.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, 5-phenyl-1H-pyrrole-3-carbaldehyde (342 mg) was dissolved in absolute tetrahydrofuran (20 mL) and sodium hydride (60% in oil, 240 mg) was added while stirring at room temperature. After stirring at the same temperature for 15 min, 15-crown-5 (1.21 mL) was added, and the mixture was further stirred at the same temperature for 15 min. Pyridin-3-ylsulfonyl chloride hydrochloride (642 mg) was added, and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→1:1) to give the title compound as a brown solid (yield 470 mg, 75%).

Workup

  1. stirringAfter stirring at the same temperature for 15 min
  2. stirringthe mixture was further stirred at the same temperature for 15 min
  3. stirringthe mixture was further stirred at the same temperature for 30 min
  4. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→1:1)

Sources & evidence

ORD record
ord-360c18fa02c94ed3b44fdf4dccf51ee3
Source dataset
uspto-grants-2011_07
Patent number
US07977488B2

Reaction notes

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