Sodium hydride → HCID 86232843, compound

HRID 554322Notes

Reaction equation

HRID 554322 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.[S:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[CH:33]=[C:32]1[S:40](Cl)(=[O:42])=[O:41]>O1CCCC1.[Cl-].[Na+].O>[S:31]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[CH:33]=[C:32]1[S:40]([N:11]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][C:9]([CH:12]=[O:13])=[CH:10]1)(=[O:42])=[O:41]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27763331-Benzothiophene-2-sulfonyl chlorideHCID 110520905-Phenyl-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 86232843HCID 86232843, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (10 mL) of 5-phenyl-1H-pyrrole-3-carbaldehyde (100 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 47 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (257 mg) was added dropwise and the mixture was stirred for 30 min, 2-benzothiophenesulfonyl chloride (204 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→3:2) to give the title compound as a colorless oil (yield 180 mg, 84%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was further stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with 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 (eluent: hexane-ethyl acetate=4:1→3:2)

Sources & evidence

ORD record
ord-e3f87e923eec40c0bc5c5ff509f5f7a3
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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