Reaction #641504

Reaction equation

2-benzothiophenesulfonyl chloride

15-Crown-5

5-phenyl-1H-pyrrole-3-carbaldehyde

sodium hydride

→

title compound

Yield 84.0%

1-(1-Benzothien-2-ylsulfonyl)-5-phenyl-1H-pyrrole-3-carbaldehyde

Yield 84.0%

Solvents

brine

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred for 30 min
2. 2
   workup.STIRRINGthe mixture was further stirred for 1 hr
3. 3
   Extractionthe mixture was extracted with ethyl acetate
4. 4
   WashThe extract was washed with saturated brine
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→3:2)

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%).

Source