Ethanol → (+/-)-1-(Biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600903Notes

Reaction equation

HRID 1600903 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[OH-].[Na+].Cl[CH2:20][CH:21]([OH:30])[CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1>O>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][C:10]([O:13][CH2:20][CH:21]([OH:30])[CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 71034-HydroxybiphenylHCID 14798Sodium HydroxideHCID 22465338HCID 22465338, compound

Product 1

HCID 11109974(+/-)-1-(Biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared according to the method described in Example 24b) from 4-phenylphenol (0.916 g), ethanol (10 ml), sodium hydroxide (0.215 g), water (5 ml) and (±)-α-(chloromethyl)-3-pyridinepropanol (1.0 g; from Example 24a) above) to give a yellow oil. This was purified by column chromatography over silica eluting with dichloromethane:ethanol (95:5) to give the title compound as a pale yellow gum which solidified on standing (0.307 g).

Workup

  1. customPrepared
  2. customto give a yellow oil
  3. customThis was purified by column chromatography over silica eluting with dichloromethane:ethanol (95:5)

Sources & evidence

ORD record
ord-cc74e78d283a4a0891612da15e0abbb7
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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