Triacetoxyperiodinane → 4-[3-(4-Isobutylphenyl)-1,2,4-oxadiazol-5-yl]benzaldehyde

HRID 2242229Notes

Reaction equation

HRID 2242229 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([CH:22]=[O:23])=[CH:20][CH:21]=3)[O:13][N:12]=2)=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59204309{4-[3-(4-Isobutylphenyl)-1,2,4-oxadiazol-5-yl]phenyl}methanol

Product 1

HCID 592043124-[3-(4-Isobutylphenyl)-1,2,4-oxadiazol-5-yl]benzaldehydeYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of {4-[3-(4-isobutylphenyl)-1,2,4-oxadiazol-5-yl]phenyl}methanol (1.30 g, 4.21 mmol) and dichloromethane (20 mL) was added to a solution of Dess-Martin periodinane (2.25 g, 5.30 mmol) and dichloromethane (20 mL) and stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethene, washed with 1 N NaOH (2×) and brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (0.333 g, 26% yield) as a white solid.

Workup

  1. additionThe reaction mixture was diluted with dichloromethene
  2. washwashed with 1 N NaOH (2×) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f17dd6ae5a542c298500f596aa71561
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

Loading…