Sodium Azide → 2-Azido-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanol

HRID 623479ノート

反応式

HRID 623479 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].Cl([O-])(=O)(=O)=O.[Li+].[O:11]1[CH2:13][CH:12]1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[N:18][CH:19]=1>C(#N)C>[N:1]([CH:12]([C:14]1[CH:19]=[N:18][C:17]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])=[CH:16][CH:15]=1)[CH2:13][OH:11])=[N+:2]=[N-:3]

参加物

5

反応物 3

HCID 33557Sodium AzideHCID 23665649Lithium perchlorateHCID 874265125-(Oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine

生成物 1

HCID 1317351792-Azido-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanol収率 37%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Sodium azide (1.05 g, 16.2 mmol) and lithium perchlorate (6.45 g, 60.7 mmol) are added to a solution of 5-(oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine (0.89 g, 4.04 mmol, Step-5, single enantiomer) in acetonitrile (100 mL) is refluxed with stirring for 5 hours. White precipitate is filtrated and filtrate is concentrated in vacuo. The residue is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1) to give 0.39 g (37% yield) of the title compound as colorless oil.

後処理

  1. temperatureis refluxed
  2. filtrationWhite precipitate is filtrated
  3. concentrationfiltrate is concentrated in vacuo
  4. additionThe residue is poured into water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-659ebd49bbab4b7985d88178920293ae
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

反応ノート

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