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

HRID 1600968
ノート
印刷プレビュー

反応式

HRID 1600968 の反応式
[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
参加物反応条件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 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-afdf9e1b86284e5984ea0d14d1cb1624
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…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート