Isoprene → HCID 565258, compound

HRID 2254035Notes

Reaction equation

HRID 2254035 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[CH2:6]([O:8][C:9](=[O:17])[C:10](=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:7]>[I-].[Zn+2].[I-]>[CH3:5][C:3]1[CH2:4][C:10]([C:9]([O:8][CH2:6][CH3:7])=[O:17])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:16][CH2:1][CH:2]=1

Participants

4

Reactant 2

HCID 6557IsopreneHCID 691051,3-Diethyl 2-oxopropanedioate

Product 1

HCID 565258HCID 565258, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

To 50 g (0.70 mol) isoprene was added 25 g (0.14 mol) diethylketomalonate and 0.78 g (2.4 mmol) zinc iodide. The reaction mixture was stirred at room temperature for 48 hours. The excess isoprene was removed under vacuum. Flash chromatography in 20:1 hexanes:ethyl acetate yielded 1.2 g of oil.

Workup

  1. customThe excess isoprene was removed under vacuum

Sources & evidence

ORD record
ord-da1c56ff4a614b4ba27ce6cb80db3459
Source dataset
uspto-grants-1993_08
Patent number
US05234900

Reaction notes

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