Ethyl diazoacetate → Ethyl chrysanthemate

HRID 247733

Reaction equation

HRID 247733 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(Cl)Cl>[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

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 12992Biisocrotyl

Product 1

HCID 7334Ethyl chrysanthemate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl diazoacetate (5.0 g) in methylene chloride (50 mL) was added dropwise to a slurry of the Cu,K-PFIEP[SO3H] catalyst described above (2.0 g) in methylene chloride (100 mL) and 2,5-dimethyl-2,4-hexadiene (8.33 g). After stirring for about 18 h at ambient temperature, the reaction product was isolated by filtering off the catalyst, evaporating the solvent and chromatographing the resulting residue on silica with 10% ethyl acetate and 90% hexane as eluant. The isolated chrysanthemumate had an identical 1H nmr spectrum to a commercial sample. Anal. Calcd. for C12H20O2 : C, 73.43; H, 10.27; Found: C, 74.08; H, 10.58.

Workup

  1. customthe reaction product was isolated
  2. filtrationby filtering off the catalyst
  3. customevaporating the solvent and chromatographing the resulting residue on silica with 10% ethyl acetate and 90% hexane as eluant

Sources & evidence

ORD record
ord-9775878d627b4c1b8de3c0e590bcda47
Source dataset
uspto-grants-1987_11
Patent number
US04709085

Linked notes

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