[4-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]-2,5-dimethylphenyl]methanol → HCID 86667554, compound

HRID 85256Notes

Reaction equation

HRID 85256 reaction equation
[CH2:1]([N:5]([CH2:26][CH2:27][CH2:28][CH3:29])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH2:21][OH:22])=[C:16]([CH3:23])[CH:15]=2)=[C:8]([O:24][CH3:25])[CH:7]=1)[CH2:2][CH2:3][CH3:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:26]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH:21]=[O:22])=[C:16]([CH3:23])[CH:15]=2)=[C:8]([O:24][CH3:25])[CH:7]=1)[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 1

HCID 68009049[4-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]-2,5-dimethylphenyl]methanol

Product 1

HCID 86667554HCID 86667554, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane was dissolved 1.5 g (3.79 mmol) of [4-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]-2,5-dimethylphenyl]methanol, and 6.6 g of active manganese dioxide was added thereto. The mixture was stirred at room temperature for 21 hours. After the reaction mixture was filtrated and concentrated, the residue was dissolved in 50 ml of ether. 60 mg of iodine pieces were added thereto, and the reaction mixture was stirred. The reaction mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution, and dried over anhydrous magnesium sulfate. After ether was evaporated off, the residue was purified by silica gel column chromatography to give 1.09 g of a reddish orange crystal (yield: 72.4%).

Workup

  1. additionwas added
  2. filtrationAfter the reaction mixture was filtrated
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in 50 ml of ether
  5. addition60 mg of iodine pieces were added
  6. stirringthe reaction mixture was stirred
  7. washThe reaction mixture was washed with a 5% sodium bisulfite solution
  8. dry with materialwith a saturated saline solution, and dried over anhydrous magnesium sulfate
  9. customAfter ether was evaporated off
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-44ea812f459b4dd79282135e908c02ec
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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