Hydrochloric Acid → HCID 86620749, compound

HRID 554314Notes

Reaction equation

HRID 554314 reaction equation
[CH3:1][C:2]1[C:3]([C:23](OCC)=[O:24])=[CH:4][N:5]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)(=[O:15])=[O:14])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([CH:23]=[O:24])=[CH:4][N:5]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)(=[O:15])=[O:14])[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 66924870HCID 66924870, compound

Product 1

HCID 86620749HCID 86620749, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, a solution (60 mL) of ethyl 4-methyl-1-[(3-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carboxylate (2.48 g) in tetrahydrofuran was cooled to −78° C., and a 1.5 mol/L solution (13 mL) of diisobutylaluminum hydride in toluene was added dropwise over 15 min, and the mixture was further stirred at −78° C. for 30 min. 1 mol/L Hydrochloric acid (60 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetonitrile solution (100 mL), tetra-n-propylammonium perruthenate (0.21 g), N-methylmorpholine N-oxide hydrate (1.31 g) and molecular sieves 4A powder (6.0 g) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate (300 mL) was added to the residue, the suspension 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→3:1) to give the title compound as a yellow oil (yield 1.76 g, 80%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in acetonitrile solution (100 mL)
  6. additiontetra-n-propylammonium perruthenate (0.21 g), N-methylmorpholine N-oxide hydrate (1.31 g) and molecular sieves 4A powder (6.0 g) were added
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (300 mL)
  9. additionwas added to the residue
  10. filtrationthe suspension was filtered through celite, and celite
  11. washwas washed with ethyl acetate
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→3:1)

Sources & evidence

ORD record
ord-83418cb0cfec46e78e5172d51481caf9
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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