Cesium carbonate → 6-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one

HRID 339190Notes

Reaction equation

HRID 339190 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:4][C:3]1=2.[C:20]1([S:26]([O-:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:20]1([S:26]([C:6]2[CH:7]=[C:8]3[C:3](=[CH:4][CH:5]=2)[C:2](=[O:1])[CH2:11][CH2:10][CH2:9]3)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2723840Benzenesulfinic acid, sodium saltHCID 2724141Tetrabutylammonium FluorideHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 590217396-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-oneYield 43.7%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent

Procedure

Trifluoro-methanesulfonic acid 5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (13.0 g, 0.044 mole), sodium benzenesulfinate (7.25 g, 0.044 mole), 4,5-bis(diphenylphosphino, -9,9-dimethyl Xanthos (1.1 g, 0.004 mole), tris(dibenzylideneacetone) dipalladium(0) (1.0 g, 0.004 mole), cesium carbonate (5.0 g) and tetrabutylammonium fluoride (5 mL of 1M in THF) were all added to 100 mL toluene, and the reaction mixture was refluxed for four hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, and solvent was removed under reduced pressure. The resulting residue was purified by medium pressure chromatography eluting with methylene chloride to yield 5.5 g of 6-benzenesulfonyl-3,4-dihydro-2H-naphthalen-1-one. Mp: 121° C. MS: 287 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for four hours
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over magnesium sulfate, and solvent
  4. customwas removed under reduced pressure
  5. customThe resulting residue was purified by medium pressure chromatography
  6. washeluting with methylene chloride

Sources & evidence

ORD record
ord-2cb58ecf582341bbb09e8ce739da8505
Source dataset
uspto-grants-2014_11
Patent number
US08889906B2

Reaction notes

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