Magnesium Chloride → HCID 14795414, compound

HRID 330324Notes

Reaction equation

HRID 330324 reaction equation
[F:1][C:2]([F:27])([F:26])[S:3]([O:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC(C)=C)=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[Cl-].[Mg+2].[Cl-]>C(OCC)C>[F:27][C:2]([F:26])([F:1])[S:3]([O:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]3[O:19][C:10]([CH3:24])([CH3:11])[CH2:9][C:17]=3[CH:18]=2)=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 5360315Magnesium ChlorideHCID 14795413HCID 14795413, compound

Product 1

HCID 14795414HCID 14795414, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4.4 grams (0.011 mole) of 4-(trifluoromethylsulfonyloxy)-4'-(2-methyl-2-propenoxy)benzophenone and 0.05 gram (0.0005 mole) of magnesium chloride was stirred under a nitrogen atmosphere at 170°-175° C. for 20 hours. The reaction mixture was cooled to ambient temperature, and diethyl ether was added. The mixture was filtered through diatomaceous earth, and the filtrate was placed in a separatory funnel and washed with two portions of aqueous 0.5 N sodium hydroxide, three portions of water, and one portion of a saturated, aqueous, sodium chloride solution. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by centrifically accelerated, radial thin layer chromatography. Elution was accomplished using 3:1 methylene chloride:hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 1.7 grams of (4-trifluoromethylsulfonyloxyphenyl)(2,3-dihydro-2,2-dimethylbenzofuran-5-yl) ketone. The nmr spectrum was consistent with the proposed structure.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. customthe filtrate was placed in a separatory funnel
  3. washwashed with two portions of aqueous 0.5 N sodium hydroxide, three portions of water, and one portion of a saturated, aqueous, sodium chloride solution
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue
  7. customThe residue was purified
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ce018af7eb34fb381c78e34a845ccd8
Source dataset
uspto-grants-1990_01
Patent number
US04895871

Reaction notes

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