1,3-Butadiene → Cyclopropanecarboxylic acid, 2-ethenyl-, ethyl ester

HRID 1871513Notes

Reaction equation

HRID 1871513 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[N+](=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N-]>C(OCC)C.CCCCC.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH:2]([CH:3]1[CH2:4][CH:7]1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH2:1]

Participants

6

Reactant 2

HCID 78451,3-ButadieneHCID 12192Ethyl diazoacetate

Product 1

HCID 12261391Cyclopropanecarboxylic acid, 2-ethenyl-, ethyl ester

Reagents, catalysts & solvents 3

HCID 152122Dirhodium tetraacetateCatalystHCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

Butadiene (200 ml, Aldrich) condensed at -700 was transferred to a glass lined autoclave vessel and ethyl diazoacetate (20 g, 0.175 mol, Aldrich) and rhodium acetate dimer (0.3 g, Aldrich) added. The suspension was stirred in a sealed autoclave for 24 hours at ambient temperature. The contents were diluted with 2% diethyl ether in pentane and passed through a silica pad (50 g). The pad was washed with a little ethanol and further ether-pentane. The eluant containing ethanol was treated separately. The organic phases were concentrated at reduced pressure (<5°) and subjected to short path bulb to bulb disillation (90-105° at 12 mm) to give the product as a colourless liquid (14.6 g).

Workup

  1. washThe pad was washed with a little ethanol and further ether-pentane
  2. additionThe eluant containing ethanol
  3. additionwas treated separately
  4. concentrationThe organic phases were concentrated at reduced pressure (<5°)
  5. customsubjected to short path bulb to bulb disillation (90-105° at 12 mm)

Sources & evidence

ORD record
ord-495f92af6e854239b1b1e1396ce31aba
Source dataset
uspto-grants-2000_08
Patent number
US06103752

Reaction notes

Loading…