Toluene ethylacetate → 2-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzaldehyde

HRID 258469Notes

Reaction equation

HRID 258469 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:29][OH:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.CCOC(C)=O.C1(C)C=CC=CC=1>CCOC(C)=O.O=[Mn]=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH:29]=[O:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 21584019Toluene ethylacetateHCID 541888982-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzenemethanol

Product 1

HCID 536926242-(3-(3-((7-Chloro-2-quinolinyl)methoxy)phenyl)-2-propenyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the benzylic alcohol of Step 5 (2.899 g, 6.20 mmol) in EtOAc (120 mL) was added portionwise activated MnO2 (10.15 g, 114 mmol) and the reaction was followed by TLC (EtOAc:toluene 7.5:92.5). When the reaction was completed (approximately 2 h), the mixture was filtered through silica, concentrated, and the title product was purified by flash chromatography on silica using EtOAc:toluene 2.5:97.5. Yield 2.18 g, 85%.

Workup

  1. custom(approximately 2 h)
  2. filtrationthe mixture was filtered through silica
  3. concentrationconcentrated
  4. customthe title product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-711e9905547545278808a19a982ec44a
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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