Triacetoxyperiodinane → HCID 22174864, compound

HRID 1896996Notes

Reaction equation

HRID 1896996 reaction equation
[CH3:1][C:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[C:5]([CH3:16])[N:4]([C:17]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:20]=[CH:19][N:18]=2)[N:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([CH:14]=[O:15])=[CH:12][CH:13]=2)=[C:5]([CH3:16])[N:4]([C:17]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:20]=[CH:19][N:18]=2)[N:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22174860HCID 22174860, compound

Product 1

HCID 22174864HCID 22174864, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of {4-[3,5-dimethyl-1-(4-pyridin-2-yl-pyrimidin-2-yl)-1H-pyrazol-4-yloxy]-phenyl}-methanol (1.53 g, 4.10 mmol) in chloroform (80 mL) was added the Dess-Martin periodinane (2.36 g, 5.56 mmol). The reaction mixture was stirred at room temperature for 3 hours and then concentrated to provide a white paste. Flash chromatography over silica (methanol/methylene chloride) provided 1.37 g (90%) the product as a white solid. 1H NMR analysis was consistent with assigned structure.

Workup

  1. concentrationconcentrated
  2. customto provide a white paste

Sources & evidence

ORD record
ord-22cab4c40674488fa68ffa8cc1023362
Source dataset
uspto-grants-2013_08
Patent number
US08518999B2

Reaction notes

Loading…