Ethylene carbonate → HCID 53794779, compound

HRID 1388249Notes

Reaction equation

HRID 1388249 reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][O:2]1.[CH2:7]=[CH:8][CH:9]=[CH:10][CH3:11].[CH2:12](P(CC)CC)C.O1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH3:20][C:21]1[CH:8]([CH:9]=[CH:10][CH3:11])[CH2:7][CH:23]([CH3:12])[C:22]=1[C:1]([O:2][CH2:3][CH2:4][OH:5])=[O:6]

Participants

5

Reactant 4

HCID 7303Ethylene carbonateHCID 8028TetrahydrofuranHCID 15301Penta-1,3-dieneHCID 27365Triethylphosphine

Product 1

HCID 53794779HCID 53794779, compound

Conditions

Temperature
120 °C

Procedure

A 200-ml stainless steel autoclave was filled in an argon atmosphere with the following: ethylene carbonate (22.0 g, 0.25 mole), 1,3-pentadiene (E and Z mixture, 50.0 ml, 0.50 mole), tetrahydrofuran (50 ml), Ni[1,5-cyclooctadiene]2 (300 mg, 1.09 mmole) and triethylphosphine (515 mg, 4.36 mmole). The autoclave was sealed and heated to 120° C. for 18 hours. The resultant yellow-green solution was evaporated and the title compound was isolated using column chromatography. Isolated yield was 11.19 g (20 percent of theory) of an isometric mixture containing 80 percent by weight of the title compound. Analysis by nuclear magnetic resonance spectroscopy confirmed the product's identity.

Workup

  1. customThe autoclave was sealed
  2. customThe resultant yellow-green solution was evaporated

Sources & evidence

ORD record
ord-ec335cce4eb94fd69a2e99b5fde1f816
Source dataset
uspto-grants-1984_02
Patent number
US04431592

Reaction notes

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