Diethyl acetonedicarboxylate → HCID 54034256、化合物

HRID 325420

反応式

HRID 325420 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10](=O)[C:11](=[N:19]O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH3:22][CH2:23][O:24][C:25]([CH2:27][C:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=O)=[O:26].C([O-])(=O)C.[Na+]>[Zn].C(O)(=O)C>[C:15]([O:14][C:12]([C:11]1[NH:19][C:28]([CH2:27][C:25]([O:24][CH2:23][CH3:22])=[O:26])=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]=1[CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

参加物

6

反応物 3

HCID 66045Diethyl acetonedicarboxylateHCID 517045Sodium AcetateHCID 178451312HCID 178451312、化合物

生成物 1

HCID 54034256HCID 54034256、化合物収率 31%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

Crude t-butyl 5-(m-chlorophenyl)-2-hydroximino-3-oxopentanoate (43 g., 0.15 mol) and diethyl acetonedicarboxylate (28 ml, 30.3 g, 0.15 mol) are placed in a 1 liter round bottom flask and 250 ml of glacial acetic acid added. With stirring, 25 g (0.30 mol) anhydrous sodium acetate is added followed by 26 g Zn dust (94% fine, 0.364 mol) in a portionwise manner so that the exotherm does not bring the reaction to reflux. When addition is complete, the reaction is heated on a steam bath for one hour. The hot solution is then decanted from the residual zinc into 3 liters of ice water, and the resulting mixture is stirred vigorously until the oil solidifies. The mixture is then allowed to stand for 1.5 hours, and the solid is filtered. The solid is washed with water, dried in vacuo and recrystallized to give 21.5 g (31%) of ethyl 5-(t-butoxycarbonyl)-4-[2-(m-chlorophenyl)ethyl]-3-ethoxycarbonylpyrrole-2-acetate, M.P. 131°- 132°.

後処理

  1. customthe reaction
  2. temperatureto reflux
  3. additionWhen addition
  4. temperaturethe reaction is heated on a steam bath for one hour
  5. customThe hot solution is then decanted from the residual zinc into 3 liters of ice water
  6. stirringthe resulting mixture is stirred vigorously until the oil
  7. filtrationthe solid is filtered
  8. washThe solid is washed with water
  9. customdried in vacuo
  10. customrecrystallized

出典と根拠

ORDレコード
ord-505488170c2b4d528249f20b4bfb6f2c
出典データセット
uspto-grants-1984_04
特許番号
US04440779

関連ノート

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