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

HRID 1048059Notes

Reaction equation

HRID 1048059 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-dc4f2ce49e6a467ca224206b540c2891
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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