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

HRID 510664Notes

Reaction equation

HRID 510664 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-56e8a009fc404ad786e4a631758c2571
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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