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

HRID 4589

반응식

HRID 4589 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9adca82e09c421dacd1f2f89a865ee9
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727060

연결된 노트

불러오는 중…