Chloromethyl Methyl Ether → 2-Fluoro-5-(1-methoxymethoxy-ethyl)-pyridine

HRID 561007

반응식

HRID 561007 반응식
CCN(C(C)C)C(C)C.Cl[CH2:11][O:12][CH3:13].[F:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]([OH:23])[CH3:22])=[CH:17][CH:16]=1>ClCCl.C(Cl)(Cl)Cl.C(O)(C)C>[F:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]([O:23][CH2:11][O:12][CH3:13])[CH3:22])=[CH:19][N:20]=1

참가 물질

6

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 666001661-(6-Fluoropyridin-3-yl)ethan-1-ol

생성물 1

HCID 667382922-Fluoro-5-(1-methoxymethoxy-ethyl)-pyridine수율 66%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21906603Chloroform isopropyl alcohol용매

반응 조건

온도
0 °C

실험 절차

Add N,N′-diisopropylethylamine and chloromethoxymethane to a solution of 1-(6-fluoro-pyridin-3-yl)-ethanol (3.0 g, 21.3 mmol) in dichloromethane at 0° C. Continue to stir the mixture for 30 min at 0° C., then overnight at room temperature. Dilute the mixture with chloroform/isopropyl alcohol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry it over sodium sulfate. Concentrate the solution in vacuo to a dark residue. Purify by column chromatography (hexane→20% ethyl acetate in hexane) to afford the product as a colorless solid (3 g, 66%). MS (ES) m/z 186 [M+1]+.

후처리

  1. customovernight
  2. customat room temperature
  3. washWash the solution with saturated aqueous sodium chloride
  4. dry with materialDry it over sodium sulfate
  5. concentrationConcentrate the solution in vacuo to a dark residue
  6. customPurify by column chromatography (hexane→20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-fab50c36c9d14844a11c4da0c5f58bf0
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063212B2

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