(2-Chlorothiophen-3-yl)naphthalen-2-yl Methanol → (2-Chlorothiophen-3-yl)-(naphthalen-2-yl)-methanone

HRID 34010Notes

Reaction equation

HRID 34010 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[OH:8]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)=[O:8]

Participants

4

Reactant 1

HCID 23070162(2-Chlorothiophen-3-yl)naphthalen-2-yl Methanol

Product 1

HCID 23070192(2-Chlorothiophen-3-yl)-(naphthalen-2-yl)-methanoneYield 52.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1.18 g of (2-chlorothiophen-3-yl)-(naphthalen-2-yl)-methanol in 12 mL of toluene was added 1.12 g of activated manganese dioxide at room temperature, and after stirring at 50° C. for a day, manganese dioxide was filtered off through Celite. The solvent was distilled off, and the resultant crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:50), to afford 0.61 g of the title compound as a colorless oil.

Workup

  1. filtrationmanganese dioxide was filtered off through Celite
  2. distillationThe solvent was distilled off
  3. customthe resultant crude product was purified
  4. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:50)

Sources & evidence

ORD record
ord-853adcebad0e4c17ad3678e7816250a7
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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