Ethylene Glycol → 5-(1,3-Dioxolan-2-YL)-2-fluoropyridine

HRID 561011

반응식

HRID 561011 반응식
[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][OH:12].C1COCC1>C(Cl)(Cl)Cl.C(O)(C)C.O.O.[Cu](Cl)Cl>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[N:7][CH:6]=1

참가 물질

6

반응물 3

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 164142462-Fluoro-5-formylpyridine

생성물 1

HCID 601557925-(1,3-Dioxolan-2-YL)-2-fluoropyridine수율 39%

시약·촉매·용매 2

HCID 61482Cupric chloride dihydrate촉매HCID 21906603Chloroform isopropyl alcohol용매

반응 조건

온도
100 °C

실험 절차

In a pressure vessel, combine 6-fluoro-pyridine-3-carbaldehyde (4 g, 32 mmol), ethylene glycol (3 g, 48 mmol), copper (II) chloride di-hydrate (0.56 g, 3.2 mmol) and THF (10 mL). Heat the mixture at 100° C. for 1 hour. Dilute the mixture with chloroform-isopropanol (3:1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the organic layer over sodium sulfate. Concentrate the solution in vacuo to brown oil. Purify by column chromatography (20% ethyl acetate in hexane) to afford the title compound (2.1 g, 39%) as a pale yellow oil. MS (ES) m/z 170 [M+1]+.

후처리

  1. customIn a pressure vessel, combine
  2. washWash the organic phase with saturated aqueous sodium chloride and water
  3. dry with materialDry the organic layer over sodium sulfate
  4. concentrationConcentrate the solution in vacuo to brown oil
  5. customPurify by column chromatography (20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-f668c9cefe1e479794ff2c53df520d50
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063212B2

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