Ethyl Acetate → HCID 15458948, compound

HRID 2288903Notes

Reaction equation

HRID 2288903 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([S:23](Cl)(=[O:25])=[O:24])[CH:19]=[C:20]([Cl:22])[CH:21]=1.C(OCC)(=O)C>C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.OS([O-])(=O)=O.O>[Cl:22][C:20]1[CH:19]=[C:18]([S:23]([N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:24])=[O:25])[CH:17]=[C:16]([Cl:15])[CH:21]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 1545894776369-00-1

Product 1

HCID 15458948HCID 15458948, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

At room temperature, to a stirred solution of tert-butyl pyrrole-2-carboxylate (obtained from Step A) (120 mg, 0.718 mmol) dissolved in benzene (2.5 mL) was added tetra-N-butylammonium hydrogen sulfate (49 mg, 0.144 mmol) followed by 50% aqueous sodium hydroxide solution (0.72 mL). After 10 min, a solution of 3,5-dichlorobenzenesulfonyl chloride (264 mg, 1.08 mmol) dissolved in benzene (1 mL) was added dropwise via a gas-tight syringe over a 25 min period. The reaction mixture was allowed to stir overnight at room temperature. Ethyl acetate and water were added and the phases were separated. The aqueous layer was re-extracted twice with ethyl acetate and the combined organic layers were washed with water (3×) and dried over anhydrous sodium sulfate. The crude product obtained after filtration and removal of solvents by rotoevaporation was purified by flash column chromatography on silica gel eluted with 0.5-2.5% ethyl acetate in hexane to afford the title compound (104 mg), homogeneous by TLC in 10/1 hexane/ethyl acetate; 77% yield, based on starting material consumed) and recovered starting material (58 mg, 50%).

Workup

  1. additionwas added dropwise via a gas-tight syringe over a 25 min period
  2. customthe phases were separated
  3. extractionThe aqueous layer was re-extracted twice with ethyl acetate
  4. washthe combined organic layers were washed with water (3×)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe crude product obtained
  7. filtrationafter filtration and removal of solvents by rotoevaporation
  8. customwas purified by flash column chromatography on silica gel
  9. washeluted with 0.5-2.5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0d10f265072342a48c1ba4c3b37a6b3e
Source dataset
uspto-grants-2000_07
Patent number
US06090841

Reaction notes

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