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Water → 4-Cyclopropylmethoxy-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile

HRID 657494
ノート
印刷プレビュー

反応式

HRID 657494 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:22])[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:26][CH:27]1[CH2:29][CH2:28]1.O>CS(C)=O>[CH:27]1([CH2:26][O:22][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][C:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)[CH2:29][CH2:28]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 81503BromomethylcyclopropaneHCID 594425734-(4-Fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

生成物 1

HCID 594426494-Cyclopropylmethoxy-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

実験手順

500 mg of 4-(4-fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile were dissolved in 10 ml of dry dimethyl sulfoxide, treated with 190 mg of potassium hydroxide and stirred for 30 min at room temperature. Subsequently, 0.17 ml of bromomethylcyclopropane were slowly added dropwise. The reaction mixture was stirred for 24 h, treated with water and extracted with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. The crude product, a clear oil, was purified by chromatography on silica gel using HEP/EA (2:1). 510 mg of the title compound were obtained as a white solid.

後処理

  1. stirringThe reaction mixture was stirred for 24 h
  2. extractionextracted with EA
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude product, a clear oil, was purified by chromatography on silica gel using HEP/EA (2:1)

出典と根拠

ORDレコード
ord-3b8184610c2c408682f11d170eb38f11
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08076324B2

反応ノート

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