Ethanol → (2R)-1-(3'-Carboxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600966Notes

Reaction equation

HRID 1600966 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]([OH:26])[CH2:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:11][CH:10]=2)[CH:6]=CC=1)#N.[OH-:27].[Na+].[CH2:29]([OH:31])[CH3:30]>O>[C:29]([C:30]1[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]([OH:26])[CH2:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:11][CH:10]=2)[CH:4]=[CH:3][CH:1]=1)([OH:27])=[O:31]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54167436(2R)-1-(3'-cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 54073875(2R)-1-(3'-Carboxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of (2R)-1-(3'-cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol (0.60 g) and sodium hydroxide (0.696 g) in ethanol (8 ml) and water (2 ml) was heated at reflux for 10 hours. The mixture was concentrated and the residues dissolved in water and neutralised. The precipitate was filtered off and dried under vacuum to give the title compound as a white solid (0.616 g).

Workup

  1. temperatureat reflux for 10 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residues dissolved in water
  4. filtrationThe precipitate was filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d935582cdc1f4a4c962f7951b2a6484b
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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