2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → HCID 86743130, compound

HRID 1904576Notes

Reaction equation

HRID 1904576 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:15](=[O:18])[CH2:16][Cl:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH2:19]([O:21][C:22](=[O:27])/[CH:23]=[C:24](\[NH2:26])/[CH3:25])[CH3:20]>CCO>[NH2:26][C:24](=[C:23]([C:22]([O:21][CH2:19][CH3:20])=[O:27])[CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15](=[O:18])[CH2:16][Cl:17])[CH3:25]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 54129403HCID 54129403, compound

Product 1

HCID 86743130HCID 86743130, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(m-chlorophenylmethylen)-4-chloro-3-oxobutanoate (5 g) and ethyl-3-aminocrotonate (2.3 g) in EtOH (50 ml) is stirred at room temperature for four hours, then it is evaporated at reduced pressure, the residue dissolved in Et2O (70 ml) washed with water (3×20 ml), dried on Na2SO4 and purified by column-chromatography on silica gel (120 g; eluent hexane/AcOEt 60/40) to give 4.2 g of 2-amino-7-chloro-3,5-dicarboethoxy-6-oxo-4-(m-chlorophenyl)-2-heptene as an oil.

Workup

  1. customit is evaporated at reduced pressure
  2. dissolutionthe residue dissolved in Et2O (70 ml)
  3. washwashed with water (3×20 ml)
  4. customdried on Na2SO4
  5. custompurified by column-chromatography on silica gel (120 g; eluent hexane/AcOEt 60/40)

Sources & evidence

ORD record
ord-bc8265066bf445d9b51519b34f6d6c71
Source dataset
uspto-grants-1989_06
Patent number
US04839348

Reaction notes

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