Cornforth reagent → HCID 123403367, compound

HRID 2172355Notes

Reaction equation

HRID 2172355 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][CH2:35][OH:36]>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][CH2:34][CH:35]=[O:36]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 131732958HCID 131732958, compound

Product 1

HCID 123403367HCID 123403367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thereafter 2.5 equivalents of PDC (pyridinium dichromate) and 1 equivalent of 6-(2,4,4-trimethylcyclopentylidene)-hexan-1-ol in proportion 70:30 in dichloromethane are placed in a 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 70:30 of 6-(2,4,4-trimethylcyclopentylidene)-hexanal, is distilled under reduced pressure: its boiling point is 59° C. at 0.2 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 70:30 of 6-(2,4,4-trimethylcyclopentylidene)-hexanal
  6. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-99068567200241bc9f64b94fe4aaec84
Source dataset
uspto-grants-2015_06
Patent number
US09051531B2

Reaction notes

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