Sodium Hydroxide → (Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile

HRID 2902

反応式

HRID 2902 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH:7]=O)([O-:3])=[O:2].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:25][C:26]#[N:27])[CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22].[OH-].[Na+]>[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.O.ClCCl>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[C:25](/[C:17]2[CH:18]=[C:19]([O:23][CH3:24])[C:20]([O:21][CH3:22])=[C:15]([O:14][CH3:13])[CH:16]=2)\[C:26]#[N:27])[CH:9]=[CH:10][C:11]=1[CH3:12])([O-:3])=[O:2]

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 258873,4,5-TrimethoxyphenylacetonitrileHCID 17989983-Nitro-p-tolualdehyde

生成物 1

HCID 10570105(Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile収率 14.1%

試薬・触媒・溶媒 3

HCID 21218Trioctylmethylammonium chloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

5.0 g of 3-nitro-4-methylbenzaldehyde, 6.27 g of 3,4,5-trimethoxyphenylacetonitrile, 1.44 g of sodium hydroxide and 500 mg of trioctylmethylammonium chloride were dissolved in 25 ml of water and 500 ml of dichloromethane. The mixture was stirred vigorously for 3 hours at room temperature. The ice water was added to the mixture and the mixture was extracted with dichloromethane three times and dried over anhydrous sodium sulfate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (dichloromethane) to give 1.5 g of the intended compound. The yield was 14.1%.

後処理

  1. extractionthe mixture was extracted with dichloromethane three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by silica gel column chromatography (dichloromethane)

出典と根拠

ORDレコード
ord-0522bf4210474a18b5909e43c5604b2d
出典データセット
uspto-grants-1998_03
特許番号
US05731353

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