Sulfuric acid magnesium salt (1:1) → HCID 12507349, compound

HRID 648674Notes

Reaction equation

HRID 648674 reaction equation
[Cl:1][C:2]1([Cl:11])[C@H:9]2[C@H:4]([CH2:5][CH2:6][CH:7]=[CH:8]2)[C@@H:3]1[OH:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[Cl:1][C:2]1([Cl:11])[C@H:9]2[C@H:4]([CH2:5][CH2:6][CH:7]=[CH:8]2)[C:3]1=[O:10]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 14127271HCID 14127271, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 12507349HCID 12507349, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.9 g of (1R,6S,7S)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-ol, prepared as shown in Preparation 22, 9.0 g of pyridinium chlorochromate and 14 g of magnesium sulfate in 200 ml of methylene chloride under nitrogen was refluxed for 4 hours. The mixture was cooled and filtered through celite, then Florisil. Solvent was removed from the eluate under reduced pressure and the residue distilled under vacuum to give 3.1 g of (1R,6S)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one, [α]D =+71.4° C., (C=0.7, CHCl3).

Workup

  1. customprepared
  2. temperaturewas refluxed for 4 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. customSolvent was removed from the eluate under reduced pressure
  6. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-31a64a8be84a448c9cc1b04dc15c6bee
Source dataset
uspto-grants-1988_04
Patent number
US04735966

Reaction notes

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