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

HRID 1600946
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HRID 1600946 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+].[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 2724141Tetrabutylammonium FluorideHCID 218306904-(3-Hydroxymethylphenyl)phenolHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 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 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ed5b89221de43988eceff0e74d043c0
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05977105

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