Toluene → HCID 57687727, compound

HRID 2359933Notes

Reaction equation

HRID 2359933 reaction equation
[CH3:1][C:2]1[C:3]([C:22](OC)=[O:23])=[CH:4][N:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]=1[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[C:3]([CH:22]=[O:23])=[CH:4][N:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]=1[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 57687735HCID 57687735, compound

Product 1

HCID 57687727HCID 57687727, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methyl 4-methyl-1-phenyl-5-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (410 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and 1.5 mol/L toluene solution of diisobutylaluminum hydride (2.3 mL) was added dropwise. After the completion of the dropwise addition, the mixture was stirred at room temperature for 30 min. Saturated brine was added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was filtered through celite, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. A solution of the residue in acetonitrile (10 mL) was cooled to 0° C., tetra-n-propylammonium perruthenate (40 mg), N-methylmorpholine N-oxide (269 mg) and molecular sieves 4 A powder (1.0 g) were added, and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1) to give the title compound as a pale-yellow oil (yield 170 mg, 45%).

Workup

  1. additionAfter the completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. filtrationThe reaction mixture was filtered through celite
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. temperatureA solution of the residue in acetonitrile (10 mL) was cooled to 0° C.
  9. additiontetra-n-propylammonium perruthenate (40 mg), N-methylmorpholine N-oxide (269 mg) and molecular sieves 4 A powder (1.0 g) were added
  10. stirringthe mixture was stirred at room temperature for 2.5 hr
  11. concentrationThe reaction mixture was concentrated under reduced pressure
  12. filtrationfiltered through celite
  13. concentrationThe filtrate was concentrated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-e030239911df4eb5a2c2a321aa267471
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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