Chloroacetonitrile → Cyanomethyl-(alpha-naphthylmethyl)-malonic acid diethyl ester

HRID 2106961

反応式

HRID 2106961 の反応式
[C:1]([CH2:3]C(CC1C2C(=CC=CC=2)C=CC=1)C(O)=O)#[N:2].[CH2:19]([O:21][C:22](=[O:40])[CH:23]([CH2:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:20].ClCC#N.[H-].[Na+]>CN(C=O)C>[CH2:27]([O:26][C:24](=[O:25])[C:23]([CH2:3][C:1]#[N:2])([CH2:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1)[C:22]([O:21][CH2:19][CH3:20])=[O:40])[CH3:28]

参加物

6

反応物 4

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 9972002Diethyl (1-naphthyl)methylmalonateHCID 230496412(R,S)-Cyanomethyl-3-alpha-naphthylpropionic acid

生成物 1

HCID 54438257Cyanomethyl-(alpha-naphthylmethyl)-malonic acid diethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2(R,S)-Cyanomethyl-3-α-naphthylpropionic acid: 3.0 g of α-naphthylmethylmalonic acid diethyl ester and, after 30 minutes, 0.6 ml of chloroacetonitrile are added to a stirred suspension of 0.44 g of sodium hydride dispersion in 50 ml of DMF. The reaction mixture is stirred for 1 hour at 50° and then concentrated by evaporation in a high vacuum. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate, concentrated by evaporation and purified by chromatography on silica gel with toluene, yielding cyanomethyl-(α-naphthylmethyl)-malonic acid diethyl ester.

後処理

  1. concentrationconcentrated by evaporation in a high vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with 0.1N hydrochloric acid and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. custompurified by chromatography on silica gel with toluene

出典と根拠

ORDレコード
ord-649492dd713142d8b52fc300f269f0d0
出典データセット
uspto-grants-1990_06
特許番号
US04931591

関連ノート

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