Hydrochloric Acid → HCID 86620748, compound

HRID 554313Notes

Reaction equation

HRID 554313 reaction equation
[CH3:1][C:2]1[N:3]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=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].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[CH3:1][C:2]1[N:3]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 66924720HCID 66924720, compound

Product 1

HCID 86620748HCID 86620748, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution (10 mL) of ethyl 2-methyl-1-[(3-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carboxylate (588 mg) in tetrahydrofuran was cooled to −78° C., a 1.5 mol/L toluene solution (3.00 mL) of diisobutylaluminum hydride was added dropwise. After completion of the dropwise addition, the mixture was stirred at −78° C. for 30 min, and at room temperature for 30 min. 1 mol/l Hydrochloric acid (10 mL) was added to the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. A solution (10 mL) of the residue in acetonitrile was cooled to 0° C., tetra-n-propylammonium perruthenate (53 mg), N-methylmorpholine N-oxide (358 mg) and molecular sieves 4A 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 (30 mL) 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 250 mg, 48%).

Workup

  1. additionAfter completion of the dropwise addition
  2. waitat room temperature for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. temperatureA solution (10 mL) of the residue in acetonitrile was cooled to 0° C.
  8. additiontetra-n-propylammonium perruthenate (53 mg), N-methylmorpholine N-oxide (358 mg) and molecular sieves 4A powder (1.0 g) were added
  9. stirringthe mixture was stirred at room temperature for 2.5 hr
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. filtrationfiltered through celite
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-8ad4872b8e9948eb92920fae16cd14b9
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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