Ethyl diazoacetate → Ethyl chrysanthemate

HRID 2241172Notes

Reaction equation

HRID 2241172 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[CH3:9][C:10](=[CH:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:11]>C(#N)C.C1(NN)C=CC=CC=1>[CH3:8][CH2:7][O:6][C:4]([CH:3]1[C:14]([CH3:16])([CH3:15])[CH:13]1[CH:12]=[C:10]([CH3:11])[CH3:9])=[O:5]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetate2×HCID 12992Biisocrotyl

Product 1

HCID 7334Ethyl chrysanthemateYield 50.9%

Reagents, catalysts & solvents 2

HCID 7516PhenylhydrazineCatalystHCID 6342AcetonitrileSolvent4×

Conditions

Temperature
50 °C

Procedure

0.2 g of the catalyst whose preparation is described in example 44 are suspended in 3 ml of acetonitrile then 0.096 mmol (0.01 g) of phenylhydrazine in 3 ml of acetonitrile are added. The reaction mixture is heated to 50° C. and 0.1 ml of a solution containing 0.21 ml (2 mmol) of ethyl diazoacetate in 3 ml acetonitrile is added. 10 mmol of 2,5-dimethyl-2,4-hexadiene (1.4 ml) are then added, followed by the remaining 2.9 ml of the ethyl diazoacetate solution in acetonitrile, added over a period of about 1 hour. The reaction mixture is maintained under stirring at 50° C. for 6 hours. The catalyst is removed by filtration and washed with 20 ml of dichloromethane. 0.2 g of ethyl chrysanthemate are obtained.

Workup

  1. additionis added
  2. additionadded over a period of about 1 hour
  3. temperatureThe reaction mixture is maintained
  4. customThe catalyst is removed by filtration
  5. washwashed with 20 ml of dichloromethane

Sources & evidence

ORD record
ord-375cff61749e49d99b228e43875c9c2e
Source dataset
uspto-grants-2010_05
Patent number
US07723539B2

Reaction notes

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