Ethyl Acetate → (4-Hydroxyphenyl)[5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]methanone

HRID 1433840Notes

Reaction equation

HRID 1433840 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](B(O)O)[CH:7]=[CH:6]2.[CH2:16]([OH:20])[CH2:17][CH2:18]O.[C:21]([O:24][CH2:25][CH3:26])(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C>[OH:20][C:16]1[CH:17]=[CH:18][C:12]([C:3]([C:4]2[CH:26]=[C:25]([O:24][CH3:21])[CH:7]=[CH:6][C:5]=2[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)=[O:2])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 104421,3-PropanediolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 46416926-Methoxy-2-naphthaleneboronic acid

Product 1

HCID 57933864(4-Hydroxyphenyl)[5-methoxy-2-(6-methoxynaphthalen-2-yl)phenyl]methanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (6-methoxynaphthalen-2-yl)boronic acid in diethyl ether (60 ml) was added 1,3-propanediol (2.3 ml), the solution was stirred for 15 minutes at room temperature, then ethyl acetate (70 ml) was added thereto followed by stirring for 10 minutes at room temperature. To the reaction mixture was added anhydrous magnesium sulfate, the solution was stirred, then insoluble material was removed by filtration, the solvent was evaporated in vacuo. To the total amount of the resulting 2-(6-methoxynaphthalen-2-yl)[1.3.2]dioxaborinane crude product were sequentially added (2-bromo-5-methoxyphenyl)[4-(4-nitrobenzyloxy)phenyl]methanone (6.9 g), cesium carbonate (10.2 g), N,N-dimethylformamide (80 ml) and tetrakis(triphenylphosphine)palladium(0) (900 mg), and the solution was stirred for 10.5 hours at 80° C. Ethyl acetate and water were added thereto, insoluble material was removed by filtration, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (brown foam) (4.1 g).

Workup

  1. stirringby stirring for 10 minutes at room temperature
  2. stirringthe solution was stirred
  3. custominsoluble material was removed by filtration
  4. customthe solvent was evaporated in vacuo
  5. stirringthe solution was stirred for 10.5 hours at 80° C
  6. additionEthyl acetate and water were added
  7. custominsoluble material was removed by filtration
  8. extractionthe solution was extracted with ethyl acetate
  9. washsequentially washed with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated in vacuo
  12. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-80ea4fc4b9ea4d0a9008a7ff0add29f6
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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