4-Hydroxybiphenyl → HCID 18379631, compound

HRID 2299031Notes

Reaction equation

HRID 2299031 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([N:20]1[CH2:23][CH:22]([O:24]S(C)(=O)=O)[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:29]1([C:35]2[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O>[CH:7]([N:20]1[CH2:23][CH:22]([O:24][C:38]2[CH:39]=[CH:40][C:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:36][CH:37]=2)[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 18379631HCID 18379631, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.39 g, 17.4 mmol) was added to a stirred mixture of 1-benzhydryl-3-methanesulphonyloxyazetidine (J.Org.Chem., 1972, 37, 3953; 5 g, 15.8 mmol), 4-phenylphenol (2.95 g, 17.4 mmol) and anhydrous dimethylformamide (65 ml), then the resulting mixture heated under reflux for 4 hours, allowed to cool and partitioned between ethyl acetate and water. The organic phase was separated, washed with saturated brine, dried (MgSO4) and evaporated under reduced pressure, then the residue purified by flash chromatography, using hexane:ethyl acetate (95:5) as eluant, to give the title compound (1.32 g) as a colourless, amorphous solid. δ(CDCl3): 3.17 (dd,2H), 3.75 (dd,2H), 4.43 (s,2H), 4.83 (m,1H), 6.81 (d,1H), 7.16-7.55 (m,17H).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. custompartitioned between ethyl acetate and water
  5. customThe organic phase was separated
  6. washwashed with saturated brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-bf143752ba5f4f8e8ebf99806c567e3e
Source dataset
uspto-grants-2002_12
Patent number
US06495568B1

Reaction notes

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