Acetone → HCID 86613677, compound

HRID 750787Notes

Reaction equation

HRID 750787 reaction equation
[CH3:1]C(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CC(C)=O.[Br:18][C@H:19]1[C@@H:24]([OH:25])[CH2:23][C@@H:22]([C:26]([O-:28])=[O:27])[C@H:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Br:35])[CH2:20]1>O>[Br:18][C@H:19]1[C:24](=[O:25])[CH2:23][C@@H:22]([C:26]([O:28][CH3:1])=[O:27])[C@H:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Br:35])[CH2:20]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 86613678HCID 86613678, compoundHCID 131709961Jones' reagent

Product 1

HCID 86613677HCID 86613677, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Freshly prepared Jones reagent (2.7 M, 7.0 mL) was added at 0° C. to an acetone (25 mL) solution of (1R,2R,4R,5S)-4-bromo-2-(2-bromophenyl)-5-hydroxycyclohexanecarboxylate (2.50 g, 6.38 mmol) with stirring at room temperature for 40 minutes. The mixture was then diluted with water and extracted with ether (3×). The combined extracts were washed with water, saturated aqueous sodium bicarbonate and brine solutions, and dried (Na2SO4). Concentration in vacuo gave methyl (1R,2R,4R)-4-bromo-2-(2-bromophenyl)-5-oxocyclohexanecarboxylate as a colorless, thick syrup.

Workup

  1. extractionextracted with ether (3×)
  2. washThe combined extracts were washed with water, saturated aqueous sodium bicarbonate and brine solutions
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-5965c6e5736e4f71b18b6ecc15dddb68
Source dataset
uspto-grants-2008_07
Patent number
US07405229B2

Reaction notes

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