Cornforth reagent → HCID 123347450, compound

HRID 2172353Notes

Reaction equation

HRID 2172353 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][CH:23]1[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][C:24]1=[CH:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35]>ClCCl>[CH3:22][CH:23]1[CH2:27][C:26]([CH3:28])([CH3:29])[CH2:25][C:24]1=[CH:30][CH2:31][CH2:32][CH2:33][CH:34]=[O:35]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 131732957HCID 131732957, compound

Product 1

HCID 123347450HCID 123347450, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thereafter 2.5 equivalents of PDC (pyridinium dichromate) and 1 equivalent of 5-(2,4,4-trimethylcyclopentylidene)-pentan-1-ol in proportion 68:32 in dichloromethane are placed in the flask. The suspension is agitated vigorously at ambient temperature overnight. When the conversion is satisfactory (>95%), the reaction medium is filtered on Celite® and then on silica. The filtrate thus obtained is washed with an aqueous 1% HCl solution and then with a saturated aqueous sodium bicarbonate solution, and then with water. After drying on magnesium sulfate, filtration on paper and evaporation of the solvent, the crude product, containing two isomers in proportion 68:32 of 5-(2,4,4-trimethylcyclopentylidene)-pentanal, is distilled under reduced pressure: its boiling point is 52° C. at 0.3 torr.

Workup

  1. filtrationthe reaction medium is filtered on Celite®
  2. customThe filtrate thus obtained
  3. washis washed with an aqueous 1% HCl solution
  4. customAfter drying on magnesium sulfate, filtration on paper and evaporation of the solvent
  5. additionthe crude product, containing two isomers in proportion 68:32 of 5-(2,4,4-trimethylcyclopentylidene)-pentanal
  6. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-9224ae6268294a4ca8111252e843f1c0
Source dataset
uspto-grants-2015_06
Patent number
US09051531B2

Reaction notes

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