Triacetoxyperiodinane → 1-[4-(1,2,3-Thiadiazol-4-yl)phenyl]ethanone

HRID 216333Notes

Reaction equation

HRID 216333 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[S:23]1[CH:27]=[C:26]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]([OH:36])[CH3:35])=[CH:30][CH:29]=2)[N:25]=[N:24]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[S:23]1[CH:27]=[C:26]([C:28]2[CH:29]=[CH:30][C:31]([C:34](=[O:36])[CH3:35])=[CH:32][CH:33]=2)[N:25]=[N:24]1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 686676741-[4-(1,2,3-Thiadiazol-4-yl)phenyl]ethanol

Product 1

HCID 591620241-[4-(1,2,3-Thiadiazol-4-yl)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (2.1 g, 5.0 mmol) was added to an ambient temperature solution of 1-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanol (513 mg, 2.5 mmol) in methylene chloride (20 mL). After stirring at ambient temperature for 1 h, a solution of saturated aqueous sodium bicarbonate/saturated aqueous sodium thiosulfate (1:1) was added and the solution stirred until clear. The reaction mixture was extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford the title compound which was used in subsequent steps without further purification.

Workup

  1. stirringthe solution stirred until clear
  2. extractionThe reaction mixture was extracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd5231c3e81f4d219756f72ffdc68602
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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