Potassium Carbonate → 1-(5'-Ethoxymethoxy-2'methyl-2-propylbiphenyl-4-yl)propan-1-one

HRID 584287Notes

Reaction equation

HRID 584287 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:15])=[C:10](B(O)O)[CH:11]=1)[CH3:2].FC(F)(F)S(O[C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29][CH3:30])=[CH:24][C:23]=1[CH2:32][CH2:33][CH3:34])(=O)=O.[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[CH2:1]([O:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:15])=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29][CH3:30])=[CH:24][C:23]=2[CH2:32][CH2:33][CH3:34])[CH:11]=1)[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 223456045-Ethoxymethoxy-2-methylphenylboronic acidHCID 223456254-Propionyl-2-propylphenyl 1,1,1-trifluoromethanesulfonate

Product 1

HCID 223456341-(5'-Ethoxymethoxy-2'methyl-2-propylbiphenyl-4-yl)propan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.56 g (7.4 mmol) of 5-ethoxymethoxy-2-methylphenylboronic acid, 2 g (6.2 mmol) of 4-propionyl-2-propylphenyl 1,1,1-trifluoromethanesulfonate, 517 mg (12 mmol) of lithium chloride and 7.4 ml of 2M potassium carbonate solution are dissolved in 50 ml of 1,2-dimethoxyethane in a round-bottomed flask and under a stream of nitrogen. The mixture is refluxed for 10 hours. It is then poured into water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. A brown oil is obtained, which is used without further purification for the rest of the synthesis.

Workup

  1. temperatureThe mixture is refluxed for 10 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customA brown oil is obtained
  7. customwhich is used without further purification for the rest of the synthesis

Sources & evidence

ORD record
ord-38af767a9938472f8beb49ae44c4f95f
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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