HCID 18691579, compound → HCID 18691570, compound

HRID 581726Notes

Reaction equation

HRID 581726 reaction equation
[CH3:1][C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:11][OH:12].[CH3:13][C:14]1[C:15]([CH2:23][OH:24])=[CH:16][C:17]2[CH:21]=[CH:20][S:19][C:18]=2[CH:22]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH:11]=[O:12].[CH3:13][C:14]1[C:15]([CH:23]=[O:24])=[CH:16][C:17]2[CH:21]=[CH:20][S:19][C:18]=2[CH:22]=1

Participants

6

Reactant 2

HCID 18691579HCID 18691579, compoundHCID 18691580HCID 18691580, compound

Product 2

HCID 18691570HCID 18691570, compoundHCID 18691584HCID 18691584, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

In 17 ml of chloroform is dissolved 1.7 g of a mixture of 4-methylbenzo[b]thiophene-5-methanol and 6-methylbenzo[b]thiophene-5-methanol, and 4.1 g of manganese dioxide is added thereto at room temperature. Thereafter, the resulting mixture is refluxed for one hour. After the reaction, insolubles are removed from the resulting reaction mixture by filtration and the filtrate obtained is concentrated under reduced pressure. The residue obtained is purified by a moderate pressure column chromatography [eluent:hexane:toluene=1:1], to obtain 0.65 g of 4-methylbenzo[b]thiophene-5-carbaldehyde as colorless solid and 0.48 g of 6-methyl-benzo[b]thiophene-5-carbaldehyde as colorless solid.

Workup

  1. additionis added
  2. customat room temperature
  3. temperatureThereafter, the resulting mixture is refluxed for one hour
  4. customAfter the reaction, insolubles
  5. customare removed from the resulting reaction mixture by filtration
  6. customthe filtrate obtained
  7. concentrationis concentrated under reduced pressure
  8. customThe residue obtained
  9. customis purified by a moderate pressure column chromatography [eluent:hexane:toluene=1:1]

Sources & evidence

ORD record
ord-9ec7712afb7140399b410f0bb34dd80c
Source dataset
uspto-grants-1999_07
Patent number
US05922721

Reaction notes

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