Methanol → HCID 18470744, compound

HRID 2228620Notes

Reaction equation

HRID 2228620 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[NH:6][C:5]=1[C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=1)(=[O:3])[CH3:2].C[OH:25]>O>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[NH:6][C:5]=1[C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:23])=[O:25])=[CH:20][CH:21]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 54035327HCID 54035327, compound

Product 1

HCID 18470744HCID 18470744, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-acetyl-4-methyl-2-(4-methylthiophenyl)-5-(4-pyridyl)-1H-pyrrole (0.24 g, 0.74 mmol) in methanol (8 mL) was added a solution of NaIO4 (0.6 g) in water (16 mL) at room temperature. After stirring for 15 hours, the precipitates were collected by filtration. The filtrate was extracted with CH2Cl2—EtOH (10:1, 50 mL×2), dried over MgSO4, and concentrated ini vacuo. The solids were purified by flash chromatography eluting with CH2Cl2—EtOH (10:1) to provide the title compound (0.24 g, quantitative yield).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. extractionThe filtrate was extracted with CH2Cl2—EtOH (10:1, 50 mL×2)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated ini vacuo
  5. customThe solids were purified by flash chromatography
  6. washeluting with CH2Cl2—EtOH (10:1)

Sources & evidence

ORD record
ord-4ffbbe073fb145c4bd0667843fc68095
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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