Ethyl diazoacetate → Ethyl chrysanthemate

HRID 247732

Reaction equation

HRID 247732 reaction equation
[CH3:1][C:2](=[CH:4][CH:5]=[C:6]([CH3:8])[CH3:7])[CH3:3].[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>C(Cl)Cl>[CH3:16][CH2:15][O:14][C:12]([CH:11]1[C:6]([CH3:8])([CH3:7])[CH:5]1[CH:4]=[C:2]([CH3:3])[CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 12992Biisocrotyl

Product 1

HCID 7334Ethyl chrysanthemateYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A flask was charged with CH2Cl2 (25 mL), 2,5-dimethyl-2,4-hexadiene (25 mL) and 0.45 g of the Cu,K-PFIEP[SO3H] catalyst, prepared as described above. A solution of ethyl diazoacetate (2.5 g) in CH2Cl2 (25 mL) was added slowly dropwise and the resulting reaction mixture was stirred for 24 hours at ambient temperature. Gas chromatography analysis showed that the resulting product contained cis- and trans-ethyl chrysanthemumates in a 1:1.66 isomer ratio and a combined yield of 89.6%.

Workup

  1. customprepared
  2. customthe resulting reaction mixture

Sources & evidence

ORD record
ord-5b3398a32e804dbd8c4f7bb4716c2929
Source dataset
uspto-grants-1987_11
Patent number
US04709085

Linked notes

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