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

HRID 1600985
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인쇄 미리보기

반응식

HRID 1600985 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228
Dimethylformamide
용매
HCID 8028Tetrahydrofuran용매
HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2b56b1cbd8aa4f779e5b14d1cbbb1377
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05977105

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