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

HRID 1600983Notes

Reaction equation

HRID 1600983 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+].[Cl:32][C:33]1[CH:38]=[C:37](O)[CH:36]=[CH:35][C:34]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[Cl:32][C:33]1[CH:38]=[C:37]([O:10][CH2:11][C@H:12]([OH:21])[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:36]=[CH:35][C:34]=1[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 796882-Chloro-4-biphenylolHCID 2724141Tetrabutylammonium FluorideHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

Product 1

HCID 53885066(2R)-1-(2-Chlorobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolYield 11.2%

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 (0.8 g), sodium hydride (60% dispersion in mineral oil, 0.10 g) and 2-chlorobiphenyl-4-ol (0.50 g) in dimethylformamide (15 ml). The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride (1.0 g) was added. The reaction was stirred at room temperature for 5 hours and was then poured into brine and extracted with ether. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase HPLC to give the title compound as a colourless gum (0.073 g).

Workup

  1. customPrepared
  2. extractionextracted with ether
  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 reverse phase HPLC

Sources & evidence

ORD record
ord-85a86ce5042c4934a600f0576bfb794c
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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