Ethyl diazoacetate → Ethyl 2-(4-chlorophenyl)cyclopropanecarboxylate

HRID 1021431Notes

Reaction equation

HRID 1021431 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[CH2:7][CH:12]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 140854-Chlorostyrene

Product 1

HCID 533756Ethyl 2-(4-chlorophenyl)cyclopropanecarboxylateYield 9.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-chlorostyrene (1.20 ml, 10.0 mmol), Rh2(OAc)4 (0.221 g, 0.500 mmol), and toluene (20 ml) was added ethyl diazoacetate (1.09 ml, 10.50 mmol). Gas evolution was observed. The mixture was heated to 80° C. for 1 hour. The mixture was purified on silica gel (EtOAc in hexanes gradient) to provide 0.216 g of the title compound as an oil (9%).

Workup

  1. customThe mixture was purified on silica gel (EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-d3ab894a072449f69d90d0ecc76fddfc
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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