Water → (2R)-4-(3-Pyridyl)-2-benzoyloxy-1-(3'-cyanobiphenyl-4-yloxy)butane

HRID 1600914Notes

Reaction equation

HRID 1600914 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].C1(C)C=CC(S(O[CH2:28][C@H:29]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:30][CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)(=O)=O)=CC=1.O>CN(C)C=O>[N:34]1[CH:35]=[CH:36][CH:37]=[C:32]([CH2:31][CH2:30][C@@H:29]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:28][O:15][C:12]2[CH:13]=[CH:14][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)=[CH:10][CH:11]=2)[CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 37790963-(4-Hydroxyphenyl)benzonitrileHCID 53780759(2R)-2-Benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate

Product 1

HCID 53808556(2R)-4-(3-Pyridyl)-2-benzoyloxy-1-(3'-cyanobiphenyl-4-yloxy)butaneYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid 3'-cyanobiphenyl-4-ol (0.20 g, Example 36b)) was added to a suspension of sodium hydride (60%, 0.049 g) in dimethylformamide (5 ml) and the resulting solution stirred for 30 minutes. Solid (2R)-2-benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.43 g) was then added and the mixture stirred at 60° C. for 2 hours. The mixture was cooled, poured into water (50 ml) and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained was purified by column chromatography over silica eluting with diethyl ether to give the sub-title compound as an oil (0.34 g).

Workup

  1. stirringthe mixture stirred at 60° C. for 2 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by column chromatography over silica eluting with diethyl ether

Sources & evidence

ORD record
ord-0b8d4c95eeaa43cf8c15ddc2afb1534a
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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