Ethyl vinyl ether → 1-(6-Ethoxy-5,6-dihydro-4H-1,2-oxazin-3-yl)ethan-1-one

HRID 4276

反応式

HRID 4276 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]([O:9][CH2:10][CH3:11])=[CH2:8].Cl[CH2:13][C:14](=[N:18][OH:19])[C:15](=[O:17])[CH3:16]>>[CH2:7]([O:9][CH:10]1[O:19][N:18]=[C:14]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:11]1)[CH3:8]

参加物

4

反応物 3

HCID 8023Ethyl vinyl etherHCID 10340Sodium CarbonateHCID 573484271-Chloro-3-(hydroxyimino)butan-2-one

生成物 1

HCID 127214281-(6-Ethoxy-5,6-dihydro-4H-1,2-oxazin-3-yl)ethan-1-one収率 98%

実験手順

A 1000 ml three-neck flask equipped with a mechanical stirrer, a reflux condenser, and a nitrogen inlet adapter was heat dried and charged with nitrogen. When the flask was at room temperature, it was loaded in order: 39.5 g (0.37 mole) of anhydrous sodium carbonate; (with stirring) 132 g (1.83 mole) of ethyl vinyl ether; and (portionwise over a period of 7 minutes) 10.0 g (0.074 mole) of 1-chlorobutan-2,3-dione-2-oxime [Oglobin et al., J. Gen. Chem. U.S.S.R. 34, 2710 (1964)]. Stirring was continued for 21 hours. The reaction mixture was filtered, the solid cake rinsed with diethyl ether, and the combined filtrate and rinses were evaporated under reduced pressure (bath temperature maintained at <40° C.). There was obtained 12.4 g (98%) of the title compound as an oil; nmr spectroscopy indicated it to be essentially 100% pure. This procedure is essentially that described by T. L. Gilchrist, G. M. Iskander and A. K. Yagoub (J. Chem. Soc., Chem. Commun. 1981, 696-698).

後処理

  1. customA 1000 ml three-neck flask equipped with a mechanical stirrer, a reflux condenser, and a nitrogen inlet adapter
  2. temperaturewas heat
  3. customdried
  4. additioncharged with nitrogen
  5. customwas at room temperature
  6. filtrationThe reaction mixture was filtered
  7. washthe solid cake rinsed with diethyl ether
  8. customthe combined filtrate and rinses were evaporated under reduced pressure (bath temperature maintained at <40° C.)

出典と根拠

ORDレコード
ord-9620239eddff4d22a6ab98be1c6bb71f
出典データセット
uspto-grants-1988_02
特許番号
US04725599

関連ノート

読み込み中…