Diethyl acetonedicarboxylate → HCID 54034256, 화합물

HRID 325420

반응식

HRID 325420 반응식
[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]

참가 물질

6

반응물 3

HCID 66045Diethyl acetonedicarboxylateHCID 517045Sodium AcetateHCID 178451312HCID 178451312, 화합물

생성물 1

HCID 54034256HCID 54034256, 화합물수율 31%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-505488170c2b4d528249f20b4bfb6f2c
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04440779

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