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

HRID 561011

反応式

HRID 561011 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 61482Cupric chloride dihydrate触媒HCID 21906603Chloroform isopropyl alcohol溶媒

反応条件

温度
100 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-f668c9cefe1e479794ff2c53df520d50
出典データセット
uspto-grants-2011_11
特許番号
US08063212B2

関連ノート

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