Ammonium Chloride → 4-(3-Fluoro-4-methoxyphenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

HRID 657492ノート

反応式

HRID 657492 の反応式
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[O:12]=[C:13]1[CH2:18][CH2:17][C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:19]#[N:20])[CH2:15][CH2:14]1.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:13]2([OH:12])[CH2:18][CH2:17][C:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:19]#[N:20])[CH2:15][CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 178491915HCID 178491915、化合物

生成物 1

HCID 594426104-(3-Fluoro-4-methoxyphenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under an argon atmosphere, 15 ml of 3-fluoro-4-methoxyphenylmagnesium bromide solution (0.5 M in THF) were dissolved in 15 ml of dry THF in a dried two-necked flask equipped with a reflux condenser, and subsequently 1.5 g of 4-oxo-1-phenylcyclohexanecarbonitrile in the form of a suspension in 10 ml of THF were slowly added dropwise at room temperature. A precipitate was formed in the course of this. The reaction solution was heated under reflux for 2 h, subsequently added to ice water, treated with saturated ammonium chloride solution and extracted three times with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. The residue was purified chromatographically (HEP/EA 2:1) on silica gel. 950 mg of the title compound were obtained as a white solid.

後処理

  1. customequipped with a reflux condenser
  2. customA precipitate was formed in the course of this
  3. temperatureThe reaction solution was heated
  4. temperatureunder reflux for 2 h
  5. extractionextracted three times with EA
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified chromatographically (HEP/EA 2:1) on silica gel

出典と根拠

ORDレコード
ord-2db24f1ec0d94b8da41144301aa5c38d
出典データセット
uspto-grants-2011_12
特許番号
US08076324B2

反応ノート

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