Sodium Hydroxide → (+/-)-1-(4'-(2-Propenyl)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600902Notes

Reaction equation

HRID 1600902 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[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.C(OCC)C.CO>C(O)C.O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:20][CH:21]([OH:30])[CH2:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 218306924'-(2-Propenyl)biphenyl4-olHCID 21864698Diethyl ether methanolHCID 22465338HCID 22465338, compound

Product 1

HCID 21830717(+/-)-1-(4'-(2-Propenyl)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolYield 13.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 4'-(2-propenyl)biphenyl4-ol (1.22 g; Biochemistry 1987, 26(18), 5908) in ethanol (10 ml) at room temperature was treated with a solution of sodium hydroxide (0.215 g) in water (5 ml) and was then heated at reflux. A solution of (±)-α-(chloromethyl)-3-pyridinepropanol (1.0 g) in ethanol (5 ml) was added to the latter and the resulting mixture heated at reflux for 2 hours. The reaction mixture was cooled and then concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (95:5) to give a solid. Trituration with diethyl ether:methanol (9:1) gave the title compound as a colourless solid (0.256 g).

Workup

  1. temperaturewas then heated
  2. temperatureat reflux
  3. temperaturethe resulting mixture heated
  4. temperatureat reflux for 2 hours
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (95:5)
  8. customto give a solid

Sources & evidence

ORD record
ord-433f31ffb50e475bbf9b740429eaa95d
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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