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Sodium hydride → (2R)-4-(3-Pyridyl)-1-(6-(3,3,3-trifluoropropoxy)naphthalen-2-yloxy)-2-butanol

HRID 1600968
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HRID 1600968 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH:8]=2)[CH:3]=1.C1(C)C=CC(S(O[CH2:29][C@H:30]([O:39][Si](C(C)(C)C)(C)C)[CH2:31][CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)(=O)=O)=CC=1.[H-].[Na+].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.O>[N:35]1[CH:36]=[CH:37][CH:38]=[C:33]([CH2:32][CH2:31][C@@H:30]([OH:39])[CH2:29][O:1][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][C:15]([F:16])([F:17])[F:18])[CH:8]=3)[CH:3]=2)[CH:34]=1
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참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 218307112-Hydroxy-6-(3,3,3-trifluoropropoxy)naphthaleneHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

생성물 1

HCID 54174222(2R)-4-(3-Pyridyl)-1-(6-(3,3,3-trifluoropropoxy)naphthalen-2-yloxy)-2-butanol수율 64.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

Prepared according to the method described in example 26e) from 2-hydroxy-6-(3,3,3-trifluoropropoxy)naphthalene (0.212 g), (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.30 g) and sodium hydride (60%, 33 mg) in dimethylformamide (3 ml) with heating at 60° C. for 2 hours. The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride hydrate (0.30 g) was added. After 2 hours, the mixture was diluted with water and extracted with ether. The 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 hexane:acetone (3:2) to give the title compound (0.18 g) which was recrystallised from ethyl acetate:hexane.

후처리

  1. customPrepared
  2. extractionextracted with ether
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica eluting with hexane:acetone (3:2)

출처 및 근거

ORD 기록
ord-afdf9e1b86284e5984ea0d14d1cb1624
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05977105

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