Benzenesulfonyl chloride → HCID 66925014, compound

HRID 554276Notes

Reaction equation

HRID 554276 reaction equation
[F:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][N:5]([S:41]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:43])=[O:42])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 66924945HCID 66924945, compound

Product 1

HCID 66925014HCID 66925014, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (10 mL) of ethyl 4-fluoro-5-phenyl-1H-pyrrole-3-carboxylate (100 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 52 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (284 mg) was added dropwise and the mixture was stirred for 30 min. Benzenesulfonyl chloride (151 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=9:1) to give the title compound as a colorless oil (yield 60 mg, 38%).

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=9:1)

Sources & evidence

ORD record
ord-9990d6bc571f44ac8869f3d69e6857bf
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

Loading…