1-(2-Bromo-4-fluoro-phenyl)-butane-1,4-diol → 2-(2-Bromo-4-fluoro-phenyl)-tetrahydro-furan

HRID 558135

反応式

HRID 558135 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:14])[CH2:10][CH2:11][CH2:12]O>ClCCCl.C(Cl)(Cl)Cl.CC(O)C.F[Sb-](F)(F)(F)(F)F.[Ag+].[Pt](Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:10][CH2:11][CH2:12][O:14]1

参加物

6

反応物 1

HCID 574450901-(2-Bromo-4-fluoro-phenyl)-butane-1,4-diol

生成物 1

HCID 574450912-(2-Bromo-4-fluoro-phenyl)-tetrahydro-furan収率 77.3%

試薬・触媒・溶媒 4

HCID 2770Platinous chloride触媒HCID 16687962Silver hexafluoroantimonate触媒HCID 111,2-Dichloroethane溶媒HCID 21906603Chloroform isopropyl alcohol溶媒

反応条件

温度
110 °C

実験手順

Combine 1-(2-bromo-4-fluoro-phenyl)-butane-1,4-diol (1 g, 3.8 mmol), silver (I)hexafluoroantimonate (131 mg, 0.4 mmol), platinum(II) chloride (40 mg, 0.2 mmol) in 1,2-dichloroethane (10 mL) in a pressure tube. Seal the tube and heat the mixture overnight at 110° C. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with aqueous saturated sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (20% ethyl acetate in hexane) to give the title compound as a pale yellow oil (0.72 g, 77%).

後処理

  1. customSeal the tube
  2. washWash the organic phase with aqueous saturated sodium chloride and water
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify by column chromatography (20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-95ac991e75c34e8f80fa54d834ab4ec3
出典データセット
uspto-grants-2011_11
特許番号
US08063035B2

関連ノート

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