(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)methanol → 5-(2,5-Dimethyl-1H-pyrrol-1-YL)thiazole-4-carbaldehyde

HRID 1170902Notes

Reaction equation

HRID 1170902 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[S:12][CH:11]=[N:10][C:9]=2[CH2:13][OH:14])[C:4]([CH3:7])=[CH:5][CH:6]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:7][C:4]1[N:3]([C:8]2[S:12][CH:11]=[N:10][C:9]=2[CH:13]=[O:14])[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 59553888(5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)methanol

Product 1

HCID 595538795-(2,5-Dimethyl-1H-pyrrol-1-YL)thiazole-4-carbaldehydeYield 20.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazol-4-yl)methanol (86 mg, 0.41 mmol) in methylene chloride was added manganese dioxide (359 mg, 4.13 mmol). The reaction was warmed up to reflux for 3 h. The crude mixture was purified with silica gel chromatography to give an oil of 5-(2,5-dimethyl-1H-pyrrol-1-yl)thiazole-4-carbaldehyde (17 mg). 1H NMR (400 MHz, CDCl3) δ 9.72 (s, 1H), 8.87 (s, 1H), 5.98 (s, 2H), 2.05 (s, 6H). MS m/z 207.2 (M+H)+.

Workup

  1. temperatureThe reaction was warmed up
  2. temperatureto reflux for 3 h
  3. customThe crude mixture was purified with silica gel chromatography

Sources & evidence

ORD record
ord-18f69bb46a5442ac8066f381d4747f40
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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