Triacetoxyperiodinane → 2-(4-Chlorophenyl)-4,4-dimethyl-1-cyclohexene-1-carboxaldehyde

HRID 1968618Notes

Reaction equation

HRID 1968618 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[CH2:16][OH: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[CH:16]=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66713205HCID 66713205, compound

Product 1

HCID 872794142-(4-Chlorophenyl)-4,4-dimethyl-1-cyclohexene-1-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of EXAMPLE 30D (1.25 g) in dichloromethane (20 ml) was slowly added Dess-Martin Periodinane (2.78 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, filtered, 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. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 0-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-e634af2333874a42a70a78fe6d44f4c6
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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