Triacetoxyperiodinane → HCID 87562064, compound

HRID 2039977Notes

Reaction equation

HRID 2039977 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:26])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C>[CH:2]([C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:26])[C:12]2[CH:13]=[CH:14][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[CH3:9])=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58564709HCID 58564709, compound

Product 1

HCID 87562064HCID 87562064, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reactor is charged with 150 mg (0.42 mmol) of the solid obtained in step 1 and 216 mg (0.5 mmol) of the Dess-Martin reagent in 5 ml acetonitrile. The mixture is stirred at room temperature for 16 hours. The insoluble compounds are filtered and the filtrate is concentrated under reduced pressure. The obtained solid is washed with ethylic ether and pentane to give the required aldehyde (120 mg, 82%).

Workup

  1. filtrationThe insoluble compounds are filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. washThe obtained solid is washed with ethylic ether and pentane

Sources & evidence

ORD record
ord-214c45dbb76346e49cca51e61aba821b
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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