Water → HCID 86232774, compound

HRID 554316Notes

Reaction equation

HRID 554316 reaction equation
[CH3:1][C:2]1[N:3]([S:18]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)(=[O:20])=[O:19])[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7](OCC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C.O.C(OCC)(=O)C>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([S:18]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)(=[O:19])=[O:20])[C:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][C:6]=1[CH:7]=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 66924819HCID 66924819, compound

Product 1

HCID 86232774HCID 86232774, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution (15 mL) of ethyl 2-methyl-5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carboxylate (980 mg) in tetrahydrofuran was cooled to −78° C., a 1.5 mol/L solution (5.3 mL) of diisobutylaluminum hydride in toluene was added dropwise over 10 min, and the mixture was warmed to 0° C. over 2 hr. Water (100 mL) and ethyl acetate (20 mL) were added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was filtered through celite, and the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetonitrile solution (25 mL), tetra-n-propylammonium perruthenate (93 mg), N-methylmorpholine N-oxide hydrate (466 mg) and molecular sieves 4A powder (500 mg) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate (30 mL) was added to the residue. The mixture was filtered through celite, and celite was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1) to give the title compound as a yellow oil (yield 235 mg, 27%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in acetonitrile solution (25 mL)
  7. additiontetra-n-propylammonium perruthenate (93 mg), N-methylmorpholine N-oxide hydrate (466 mg) and molecular sieves 4A powder (500 mg) were added
  8. stirringthe mixture was stirred at room temperature for 2 hr
  9. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate (30 mL)
  10. additionwas added to the residue
  11. filtrationThe mixture was filtered through celite, and celite
  12. washwas washed with ethyl acetate
  13. concentrationThe filtrate was concentrated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1)

Sources & evidence

ORD record
ord-aec351e3d1d748e381717ed964ec121a
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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