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

HRID 15858Notes

Reaction equation

HRID 15858 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-bb98a432677b40e8a5f9d2cf4110463e
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Reaction notes

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