HCID 23130675, compound → HCID 58388066, compound

HRID 2080266Notes

Reaction equation

HRID 2080266 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[OH:12])=[CH:7][C:6]=1[CH3:23])[CH2:2][CH2:3][CH3:4].O(C1C=C(C=CC=1)CNC(C1C=C2C(=CC=1)NC=C2)=O)C1C=CC=CC=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)=[O:12])=[CH:7][C:6]=1[CH3:23])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 23130675HCID 23130675, compoundHCID 58388001HCID 58388001, compound

Product 1

HCID 58388066HCID 58388066, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of (4butyl-3-methyl-phenyl)-quinoline-6-yl-methanol described in Preparation Example Z+-1 (152 mg, 0.50 mmol) in chloroform (1.0 mL) was added active manganese dioxide (510 mg, 5.0 mmol), and the solution was stirred at room temperature for 5 hours. Manganese dioxide was removed by filtering through Celite pad, the filtrate was concentrated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and the title compound (56 mg, 37%) was obtained as a pale yellow oil.

Workup

  1. customManganese dioxide was removed
  2. filtrationby filtering through Celite pad
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-0b04143d72584701aedc2552fa53e040
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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