Ethyl diazoacetate → HCID 117795939, compound

HRID 1479163Notes

Reaction equation

HRID 1479163 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[CH3:18])=[CH:12][CH:11]=1>C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[C@H:17]([CH3:18])[C@H:3]2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 5314327HCID 5314327, compound

Product 1

HCID 117795939HCID 117795939, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 168478Rhodium acetateCatalyst

Procedure

Ethyl diazoacetate (1.61 g, 12 mmol) was added over 90 minutes to a mixture of rhodium acetate (44 mg) in E-1-(4-chlorophenyl)-1-propene (2.243 g, 12 mmol) at 90° C. with stirring. Heating was continued for 60 minutes. On cooling the mixture was chromatographed with EtoAc/hexane to yield 170 mg of racemic ethyl (1R,2S,3S)-2-(4-chlorophenyl)-3-methyl-cyclopropanecarboxylate. (Another isomer was also isolated.)

Workup

  1. temperatureHeating
  2. temperatureOn cooling the mixture
  3. customwas chromatographed with EtoAc/hexane

Sources & evidence

ORD record
ord-e3479b12a2e2490099568c7a071b9617
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

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