Potassium Hydroxide → Dibenzyl ether

HRID 510459Notes

Reaction equation

HRID 510459 reaction equation
[OH-:1].[K+].C(P(C(C)(C)C)C1C=CC=CC=1[C:14]1[C:19](C(C)C)=[CH:18][C:17](C(C)C)=[CH:16][C:15]=1[CH:26](C)C)(C)(C)C>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:26]([O:1][CH2:26][C:15]1[CH:14]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:14]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Method C) Compound 28 was dissolved in toluene (8 mml/mmol) and to the solution was added potassium hydroxide (2 eq, 11.7N) and the solution was degassed. To the solution was added properly substituted benzyl bromide (1.1 eq), 2-di-t-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.06 eq) and tris-(dibenzylideneaceton)-dipalladium(0) (0.03 eq). The mixture was stirred at 60° C. for 1.25 hrs. The mixture was cooled to room temperature, diluted with EtOAc and washed with 5% NaHCO3 solution (10 ml/mmol). The organic layers were dried on MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give compound pure 30 in yields varying from 30-80%.

Workup

  1. customthe solution was degassed
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with 5% NaHCO3 solution (10 ml/mmol)
  4. customThe organic layers were dried on MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. customto give compound pure 30
  9. customin yields

Sources & evidence

ORD record
ord-fa9bb441bf6847bc8e7c2832fa373c65
Source dataset
uspto-grants-2015_08
Patent number
US09096612B2

Reaction notes

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