Triacetoxyperiodinane → [3-(2-Oxo-1,3-oxazolidin-3-yl)phenyl]acetaldehyde

HRID 734578Notes

Reaction equation

HRID 734578 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[OH:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([N:32]2[CH2:36][CH2:35][O:34][C:33]2=[O:37])[CH:29]=[CH:30][CH:31]=1>ClCCl>[O:37]=[C:33]1[N:32]([C:28]2[CH:27]=[C:26]([CH2:25][CH:24]=[O:23])[CH:31]=[CH:30][CH:29]=2)[CH2:36][CH2:35][O:34]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 542438113-[3-(2-Hydroxyethyl)phenyl]-1,3-oxazolidin-2-one

Product 1

HCID 57444342[3-(2-Oxo-1,3-oxazolidin-3-yl)phenyl]acetaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane, 709 mg, 1.67 mmol) was added to a solution of 3-[3-(2-hydroxyethyl)phenyl]-1,3-oxazolidin-2-one (315 mg, 1.52 mmol) in dichloromethane (10 mL). The mixture was stirred at room temperature for 30 min, then washed with aqueous sodium hydroxide solution (1M, 10 mL). The separated organic layer the latter was dried over magnesium sulfate and concentrated under reduced pressure affording the title compound in 89% yield (278 mg). The compound was used without further purification in the next step.

Workup

  1. washwashed with aqueous sodium hydroxide solution (1M, 10 mL)
  2. dry with materialThe separated organic layer the latter was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa74891301dc45f0a4299a7a77f3e6de
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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