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

HRID 1520687Notes

Reaction equation

HRID 1520687 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>[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

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66713205HCID 66713205, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of EXAMPLE 494F in dichloromethane (120 mL) at 0° C. was added Dess-Martin periodinane (17.7 g) and the reaction was allowed to warm to room temperature. The reaction was diluted with dichloromethane (200 mL), washed twice with saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated. The crude product was filtered through a silica gel plug to give the title compound.

Workup

  1. washwashed twice with saturated aqueous NaHCO3 solution and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationThe crude product was filtered through a silica gel plug

Sources & evidence

ORD record
ord-896d23d0d9624cee8e7d87726c5afa24
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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