Sodium hydride → HCID 45381710、化合物

HRID 1402883ノート

反応式

HRID 1402883 の反応式
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=[CH:17][CH:16]=1>COCCOC>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22]/[C:23](/[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:3]/[C:1]#[N:2])=[CH:19][CH:20]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22]/[C:23](/[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:3]\[C:1]#[N:2])=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2447713-(4-chlorophenyl)-1-phenylpropan-1-one

生成物 2

HCID 45381710HCID 45381710、化合物HCID 66759042HCID 66759042、化合物

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Diethyl cyanomethylphosphonate (0.8 ml) was added dropwise at rt to a slurry of sodium hydride (60% in mineral oil, 0.2 g) in anhydrous 1,2-dimethoxyethane (15 ml) under nitrogen atmosphere. The reaction mixture was stirred at rt for 1 hour and 3-(4-chlorophenyl)-1-phenylpropan-1-one (0.4 g) was added. After stirring at 80° C. for 4 h the resultant solution was poured into ice water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4), and evaporated in vacuo. The crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1) to afford (Z)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (80 mg) and (E)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (284 mg) as colourless oils.

後処理

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1)

出典と根拠

ORDレコード
ord-43a056641e3e4af3abc405aefba1f619
出典データセット
uspto-grants-2014_12
特許番号
US08912186B2

反応ノート

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