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

HRID 623479노트

반응식

HRID 623479 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-659ebd49bbab4b7985d88178920293ae
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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