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Water → 4-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile

HRID 657513
ノート
印刷プレビュー

反応式

HRID 657513 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.Br[CH2:24][CH2:25][CH:26]1[CH2:28][CH2:27]1.[H-].[Na+].O>CN(C=O)C>[CH:26]1([CH2:25][CH2:24][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)[CH2:28][CH2:27]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 24758Sodium hydride2 回HCID 22636989(2-Bromoethyl)cyclopropane2 回HCID 594425734-(4-Fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

生成物 1

HCID 594425114-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile収率 47.1%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

500 mg of the compound of Example 1, 760 mg of (2-bromoethyl)cyclopropane (Chorvat et al., J. Med. Chem. 28, 194-200 (1985)) and 122 mg of sodium hydride in 20 ml of anhydrous DMF were stirred at room temperature for 19 h. 760 mg of (2-bromoethyl)cyclopropane and 122 mg of sodium hydride were then added and the mixture was stirred at room temperature for 4 days. The reaction mixture was then treated with 100 ml of water and extracted three times with 50 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 290 mg of the title compound were obtained as a pale yellow oil.

後処理

  1. extractionextracted three times with 50 ml each of EA
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-f6ffb8353fe14f5891972cf2c9430c43
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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