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

HRID 1600924Notes

Reaction equation

HRID 1600924 reaction equation
Cl[CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.C(O)C.[OH-].[Na+]>CCCCCC>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 124650883'-Methoxy(1,1'-biphenyl)-4-olHCID 22465338HCID 22465338, compound

Product 1

HCID 21830673(+/-)-1-(3'-Methoxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Prepared according to the method described in Example 24b) from (±)-α-(chloromethyl)-3-pyridinepropanol (1.90 g), 3'-methoxybiphenyl-4-ol (2.05 g), ethanol (40 ml) and aqueous sodium hydroxide (2.1 M, 5 ml). After the reaction was complete it was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was twice purified by column chromatography over silica eluting with dichloromethane:ethyl acetate as an oil (1.35 g). A white solid was obtained after trituration with ether:hexane.

Workup

  1. customPrepared
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was twice purified by column chromatography over silica eluting with dichloromethane
  8. customA white solid was obtained after trituration with ether

Sources & evidence

ORD record
ord-aa9fb16a39c8465fb6fb3fbff1655f53
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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