Triacetoxyperiodinane → 2-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

HRID 574797Notes

Reaction equation

HRID 574797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[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][CH2:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]=2[CH:16]=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 582376912-(4-Chlorophenyl)-5,5-dimethyl-1-cyclohexene-1-methanol

Product 1

HCID 445943302-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 75C (2.8 g) in dichloromethane (50 mL) was added Dess-Martin Periodinane (5.68 g). The reaction mixture was stirred at room temperature for 3 hours and diluted with ether and washed with 5% NaOH and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography using 20% ethyl acetate in hexanes to provide the title compound.

Workup

  1. washwashed with 5% NaOH and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b9eae5b5e53845168428149c63ab76af
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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