5-Hydroxymethyl-2-(3-iodophenyl)-1,3-oxazole → 5-Formyl-2-(3-iodophenyl)-1,3-oxazole

HRID 1672826Notes

Reaction equation

HRID 1672826 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=2)=[N:5][CH:4]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([I:14])[CH:9]=2)=[N:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 673509105-Hydroxymethyl-2-(3-iodophenyl)-1,3-oxazole

Product 1

HCID 866437045-Formyl-2-(3-iodophenyl)-1,3-oxazoleYield 91.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Hydroxymethyl-2-(3-iodophenyl)-1,3-oxazole (747 mg, 2.48 mmol) obtained in Step 2 of Example 122 was dissolved in dichloromethane (30 mL), and the mixture was stirred at room temperature for 2 hours after adding manganese dioxide (2.16 g, 24.8 mmol). The solid was separated by filtration through sellite. The filtrate was concentrated, and purified by silica gel column chromatography to give 5-formyl-2-(3-iodophenyl)-1,3-oxazole (678 mg, 91%).

Workup

  1. customThe solid was separated by filtration through sellite
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9b082a3444de414e8b89be41790c295a
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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