Triacetoxyperiodinane → 4-[5-(4-Isobutylphenyl)-1,3,4-oxadiazol-2-yl]benzaldehyde
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[O:37][C:36]([C:38]3[CH:43]=[CH:42][C:41]([CH2:44][OH:45])=[CH:40][CH:39]=3)=[N:35][N:34]=2)=[CH:29][CH:28]=1)[CH:24]([CH3:26])[CH3:25]>ClCCl>[CH2:23]([C:27]1[CH:28]=[CH:29][C:30]([C:33]2[O:37][C:36]([C:38]3[CH:39]=[CH:40][C:41]([CH:44]=[O:45])=[CH:42][CH:43]=3)=[N:35][N:34]=2)=[CH:31][CH:32]=1)[CH:24]([CH3:26])[CH3:25]Participants
4
Procedure
Dess-Martin periodinane (0.576 g, 21.4 mmol) was added to a solution of {4-[5-(4-isobutylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}methanol (0.322 g, 1.04 mmol) and dichloromethane (10 mL) and stirred at room temperature for 1 hour. The reaction mixture was quenched with 1M NaOH (10 mL), stirred for 15 minutes then additional 1N NaOH (5 mL) was added. The layers were separated and the aqueous phase was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (0.322 g, 88% yield) as a white solid.
Workup
- customThe reaction mixture was quenched with 1M NaOH (10 mL)
- stirringstirred for 15 minutes
- additionadditional 1N NaOH (5 mL) was added
- customThe layers were separated
- extractionthe aqueous phase was extracted with ethyl acetate (3×)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1f9d0578d17048deb3231aaff5a442fe
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07671043B2
Reaction notes
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