Triacetoxyperiodinane → HCID 67425347, compound

HRID 1518832Notes

Reaction equation

HRID 1518832 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-5e7f403c4d0f4c8b852e80614f8d830d
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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