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

HRID 1600985
ノート
印刷プレビュー

反応式

HRID 1600985 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+].[F:32][C:33]1[CH:34]=[C:35]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[CH:37][C:38]=1O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[F:32][C:33]1[CH:34]=[C:35]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:36]=[CH:37][C:38]=1[O:10][CH2:11][C@H:12]([OH:21])[CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 2724141Tetrabutylammonium FluorideHCID 130044482-Fluoro-4-phenylphenolHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

生成物 1

HCID 53961819(2R)-1-(3-Fluorobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol収率 32.3%

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
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 (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (1.0 g), sodium hydride (60% dispersion in mineral oil, 0.115 g) and 3-fluorobiphenyl-4-ol (0.52 g) in dimethylformamide (15 ml). The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride (1.08 g) was added. The reaction was stirred at ambient temperature for 3 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 obtained was purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1) to give the title compound as a white solid (0.25 g).

後処理

  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 obtained
  7. customwas purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1)

出典と根拠

ORDレコード
ord-2b56b1cbd8aa4f779e5b14d1cbbb1377
出典データセット
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05977105

反応ノート

読み込み中…

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