Triacetoxyperiodinane → 5-(Pyridin-3-yl)thiophene-2-carbaldehyde

HRID 612753Notes

Reaction equation

HRID 612753 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([CH2:12][OH:13])=[CH:9][CH:8]=2)[CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)[CH:2]=1

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118163512-Thiophenemethanol, 5-(3-pyridinyl)-

Product 1

HCID 108994275-(Pyridin-3-yl)thiophene-2-carbaldehydeYield 56.1%

Procedure

To a solution of (5-pyridin-3-yl-thiophen-2-yl)-methanol (144 mg in 7.5 mL dry methylene chloride) was added 327 mg of the 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one and the mixture stirred at room temperature. After 4 hours, the reaction was quenched by addition of a mixture of saturated sodium bicarbonate and saturated sodium thiosulfite (1:1) and extracted with diethyl ether. The aqueous portion was extracted further with methylene chloride and the combined organics then washed with water and brine and dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 75:25; then 80:20) gave the title compound (80 mg).

Workup

  1. customthe reaction was quenched by addition of a mixture of saturated sodium bicarbonate and saturated sodium thiosulfite (1:1)
  2. extractionextracted with diethyl ether
  3. extractionThe aqueous portion was extracted further with methylene chloride
  4. washthe combined organics then washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-41fba068ab474ccfae6c72170f5599c2
Source dataset
uspto-grants-1999_12
Patent number
US06004984

Reaction notes

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