Triacetoxyperiodinane → HCID 67425347, compound

HRID 2273746Notes

Reaction equation

HRID 2273746 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[CH:16]([OH:18])[CH3:17])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][CH2:10][C:9]=2[C:16](=[O:18])[CH3:17])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67424937HCID 67424937, compound

Product 1

HCID 67425347HCID 67425347, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of EXAMPLE 253A (1.18 g) in dichloromethane (20 ml) was slowly added Dess-Martin Periodinane (2.457 g). The reaction mixture was stirred at room temperature for 3 hours and diluted with ether. The resulting mixture was washed with aqueous NaOH and water. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography, eluting with 0-100% dichloromethane in hexane to provide the title compound.

Workup

  1. washThe resulting mixture was washed with aqueous NaOH and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography
  5. washeluting with 0-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-262ace830c8c4efe8a0b7a0424c50723
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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