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

HRID 1600946
ノート
印刷プレビュー

反応式

HRID 1600946 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+].[OH:32][CH2:33][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.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[OH:32][CH2:33][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
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 218306904-(3-Hydroxymethylphenyl)phenolHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

生成物 1

HCID 53791007(2R)-1-(3'-Hydroxymethylbiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol収率 36.7%

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 (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.68 g), sodium hydride (60%, 0.073 g) and 3'-hydroxymethylbiphenyl-4-ol (0.39 g) in N,N-dimethylformamide (10 ml). The adduct was deprotected by dissolving in tetrahydrofuran (10 ml) to which tetrabutylammonium fluoride (0.93 g) was added. The reaction was stirred at ambient temperature for 1 hour, 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 (0.2 g) as a white solid.

後処理

  1. customPrepared
  2. additionwas added
  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 was purified by column chromatography over silica eluting with ethyl acetate

出典と根拠

ORDレコード
ord-0ed5b89221de43988eceff0e74d043c0
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

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