Acetonitrile → 2-Chloro-4-(3-hydroxy-cyclohexyloxy)-benzonitrile

HRID 2241829

反応式

HRID 2241829 の反応式
[CH:1]1([OH:8])[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]1.C(#N)C.[F-].[K+].F[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([Cl:23])[CH:16]=1>C(OCC)C>[Cl:23][C:17]1[CH:16]=[C:15]([O:7][CH:3]2[CH2:4][CH2:5][CH2:6][CH:1]([OH:8])[CH2:2]2)[CH:22]=[CH:21][C:18]=1[C:19]#[N:20]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 104331,3-CyclohexanediolHCID 1090002-Chloro-4-fluorobenzonitrileHCID 522689Potassium Fluoride

生成物 1

HCID 461815492-Chloro-4-(3-hydroxy-cyclohexyloxy)-benzonitrile収率 8.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

1,3-Cyclohexanediol (116 mg, 1.0 mmole) was added to a flame dried round bottom flask under nitrogen. The flask was then charged with 5 mL of dry acetonitrile, 26 mg of potassium fluoride on alumina (0.1 mmol), and 4-fluoro-2-chloro-benzonitrile (155 mg, 1.0 mmole) and heated at reflux for 16 h. Diethyl ether (15 ml) was added to the reaction mixture, which was then extracted with water (2×), dried (MgSO4) and concentrated. Purification using a chromatotron, eluting with 10% EtOAc/hex (ethylacetate and hexane) provided 22 mg of the title compound. GC/MS: 251 (M/Z for C13H14ClNO2).

後処理

  1. customdried round bottom flask under nitrogen
  2. temperatureheated
  3. temperatureat reflux for 16 h
  4. extractionwas then extracted with water (2×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification
  8. washeluting with 10% EtOAc/hex (ethylacetate and hexane)

出典と根拠

ORDレコード
ord-972f32d772e04892a3b0f04e40a8b053
出典データセット
uspto-grants-2010_03
特許番号
US07670613B2

関連ノート

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