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

HRID 1600916ノート

反応式

HRID 1600916 の反応式
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:35]=[C:36]([C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)[CH:37]=[CH:38][CH:39]=1)#[N:33].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[C:32]([C:34]1[CH:35]=[C:36]([C:40]2[CH:45]=[CH:44][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:42][CH:41]=2)[CH:37]=[CH:38][CH:39]=1)#[N:33]

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 2724141Tetrabutylammonium FluorideHCID 37790963-(4-Hydroxyphenyl)benzonitrileHCID 57045765(2S)-2-(tert-Butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

生成物 1

HCID 57040847(2S)-1-(3'-Cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol収率 60.5%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Prepared according to the method described in Example 26e) from (2S)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.46 g, Example 26d)), sodium hydride (60%, 0.056 g) and 4-(3-cyanophenyl)phenol (0.273 g) in dimethylformamide (5 ml). The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride (0.522 g) was added. The reaction was stirred at ambient temperature for 1 hour and was then poured into brine and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure. The residue obtained was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as a solid (0.22 g).

後処理

  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 obtained
  7. customwas purified by column chromatography over silica eluting with ethyl acetate

出典と根拠

ORDレコード
ord-cfe1f42e71b24896b42bd55b55c55970
出典データセット
uspto-grants-1999_11
特許番号
US05977105

反応ノート

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