Sodium hydride → (2R)-1-(4'-Cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600951Notes

Reaction equation

HRID 1600951 reaction equation
C1(C)C=CC(S([O:10][CH2:11][C@H:12]([O:21][Si](C(C)(C)C)(C)C)[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=O)=O)=CC=1.[H-].[Na+].[C:32]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)=[CH:36][CH:35]=1)#[N:33].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[C:32]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:41]=[CH:42][C:43]([O:10][CH2:11][C@H:12]([OH:21])[CH2:13][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[CH:44][CH:45]=2)=[CH:36][CH:35]=1)#[N:33]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 1406104'-Hydroxy-4-biphenylcarbonitrileHCID 2724141Tetrabutylammonium FluorideHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

Product 1

HCID 54205826(2R)-1-(4'-Cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolYield 36.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Prepared according to the method described in Example 26e) from (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.281 g), sodium hydride (60% dispersion in mineral oil, 0.056 g) and 4'-cyanobiphenyl-4-ol (0.269 g) in N,N-dimethylformamide (5 ml). The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride (0.522 g) was added. The reaction was stirred at room temperature for 1 hour and then poured into brine and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as a solid (0.081 g).

Workup

  1. customPrepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-fc378191f567478298e1f5bb19765b0b
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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