HCID 77230809, compound → HCID 77230808, compound

HRID 409027Notes

Reaction equation

HRID 409027 reaction equation
[Cl:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([CH:10]([OH:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=1>O=[Mn]=O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:14][C:5]2=[N:6][C:7]([Cl:13])=[C:8]([C:10](=[O:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 1

HCID 77230809HCID 77230809, compound

Product 1

HCID 77230808HCID 77230808, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)ethanol (5 g, 20.15 mmol) in 200 ml, of anhydrous toluene was added MnO2 (14 g, 161 mmol). The reaction was heated to reflux overnight, cooled to rt, filtered through Celite™ and rinsed with ethyl acetate. Concentration and purification by column chromatography afforded 1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)ethanone. 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.19 (s, 1H), 2.75 (s, 3H) ppm.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered through Celite™
  4. washrinsed with ethyl acetate
  5. concentrationConcentration and purification by column chromatography

Sources & evidence

ORD record
ord-2612a1a267af4a7895cdee9b113ba31a
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

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