Triacetoxyperiodinane → HCID 58124919, compound

HRID 1971698Notes

Reaction equation

HRID 1971698 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:7])[CH3:6].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.O.[O-]S([O-])(=S)=O.[Na+].[Na+]>[CH3:16][N:8]([C:5]([CH3:7])([CH2:4][CH2:3][CH:2]=[O:1])[CH3:6])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58124797HCID 58124797, compound

Product 1

HCID 58124919HCID 58124919, compoundYield 64.6%

Reagents, catalysts & solvents 3

HCID 24477Sodium ThiosulfateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 250 mg of 12d and 500 mg of sodium bicarbonate in 3 ml of THF was added 550 mg of Dess-Martin periodinane reagent. After stirring for 1 h the reaction mixture was diluted with water. A few drops of sat. aq. Na2S2O3 solution were added and stirring was prolonged for 5 min. The product was extracted into diethyl ether. The reaction mixture was filtered over decalite, washed once with 1N NaOH, once with water, dried and concentrated. The residue was purified by chromatography over silica gel, using a gradient of CH2Cl2-diethyl ether as eluent, to provide 160 mg of 12e as colorless oil;

Workup

  1. stirringstirring
  2. waitwas prolonged for 5 min
  3. extractionThe product was extracted into diethyl ether
  4. filtrationThe reaction mixture was filtered over decalite
  5. washwashed once with 1N NaOH, once with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-92c2037c59654a8ba70160015a53fb43
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…