Ethyl levulinate → trans-6-Cyano-4-(I,6-dihydro-3-methyl-6-oxopyridazin-1-yl)-2,2-dimethylchroman-3-ol

HRID 1974839

반응식

HRID 1974839 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH:7]1[O:15][CH:6]21)#[N:2].[CH3:16][C:17]1[CH:18]=[CH:19][C:20](=[O:23])[NH:21][N:22]=1.C(OCC)(=O)CCC(C)=O.O.NN.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1.O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[C@@H:7]([OH:15])[C@@H:6]2[N:21]1[C:20](=[O:23])[CH:19]=[CH:18][C:17]([CH3:16])=[N:22]1)#[N:2]

참가 물질

8

반응물 5

HCID 10883Ethyl levulinateHCID 24654Hydrazine hydrate (1:1)HCID 66854Benzyltrimethylammonium hydroxideHCID 833466-methylpyridazin-3(2H)-oneHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

생성물 1

HCID 67823752trans-6-Cyano-4-(I,6-dihydro-3-methyl-6-oxopyridazin-1-yl)-2,2-dimethylchroman-3-ol수율 38.8%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture is prepared which contains 1 g of 6-cyano-2,2-dimethyl-3,4-epoxychromane and 1.1 g of 6-methylpyridazin-3-one (prepared by the method described in J. Chem. Soc., 1947, p. 241, by reacting ethyl levulinate with hydrazine hydrate) in 10 ml of dioxane containing 0.1 ml of a 35% methanolic solution of benzyltrimethylammonium hydroxide. After 2 days at room temperature, the mixture is diluted with water and filtered, the material on the filter is dissolved in ethyl acetate, the water is then decanted and the organic phase is dried and concentrated. After recrystallization from an ethyl acetate/isopropyl ether mixture, 0.6 g of the expected product is obtained.

후처리

  1. customA mixture is prepared which
  2. customprepared by the method
  3. filtrationfiltered
  4. dissolutionthe material on the filter is dissolved in ethyl acetate
  5. customthe water is then decanted
  6. customthe organic phase is dried
  7. concentrationconcentrated
  8. customAfter recrystallization from an ethyl acetate/isopropyl ether mixture

출처 및 근거

ORD 기록
ord-b77f316b6fdf4118aa48e5154e6ea792
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05284838

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