HCID 67547192, compound → HCID 86593198, compound

HRID 2356724Notes

Reaction equation

HRID 2356724 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH2:19][OH:20])=[CH:4][CH:3]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH:19]=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67547192HCID 67547192, compound

Product 1

HCID 86593198HCID 86593198, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(5-chlorothiophen-2-yl)-2-(4-fluoro-phenyl)-4-hydroxymethyloxazole (1.44 g) and manganese dioxide (4.76 g) in tetrahydrofuran (20 ml) was refluxed for 3 hours. The reaction mixture was filtered through Cellite and the filtrate was concentrated under reduced pressure. The resulting reside was triturated with diethyl ether to obtain 5-(5-chlorothiophen-2-yl)-2-(4-fluorophenyl)-4-formyl-oxazole (943 mg) as colorless powder.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe reaction mixture was filtered through Cellite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting reside was triturated with diethyl ether

Sources & evidence

ORD record
ord-6e8abbb3c5754cd9a13c4c657d925bdc
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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