Water → Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

HRID 127019

Reaction equation

HRID 127019 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[CH2:13][CH:14]=[CH:15][CH2:16]Cl.O.CCOCC>C(O)C>[CH2:10]([O:9][C:1]([C:2]1([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:16][CH:15]1[CH:14]=[CH2:13])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 7761Diethyl MalonateHCID 151221,4-Dichloro-2-butene

Product 1

HCID 111025Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 18.4 g (2 equivalents) in 300 ml of anhydrous ethanol is added rapidly 164 g (1 equivalent) of diethyl malonate. 1,4-Dichloro-2-butene (98% mixture of cis and trans, Aldrich) (50 g, 1 equivalent) is slowly added to the warm, stirred suspension of the diethyl sodio malonate during 15 minutes after which the mixture is refluxed for 3 hours. Upon cooling, the mixture is poured into 1.2 liters of water and an oil isolated by ether extraction. The ether extract is dried over magnesium sulfate and distilled to give 1,1-bis-ethoxycarbonyl-2-vinylcyclopropane, B.P. 108°-116° C./14 mm.

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureUpon cooling
  3. extractionThe ether extract
  4. dry with materialis dried over magnesium sulfate
  5. distillationdistilled

Sources & evidence

ORD record
ord-f2bf6351d33642db97c4ba267c1af320
Source dataset
uspto-grants-1981_03
Patent number
US04254284

Linked notes

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