Styrene → Ethyl 2-phenylcyclopropane-1-carboxylate

HRID 247736Notes

Reaction equation

HRID 247736 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[C:11]1([CH:10]2[CH2:9][CH:3]2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7501StyreneHCID 12192Ethyl diazoacetate

Product 1

HCID 316914Ethyl 2-phenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction described in Example 3 was substantially repeated except that the Cu,K-PFIEP[SO3H] catalyst was replaced by the Cu,K-PFIEP[SO3H]/PFIEP[CO2H] (0.58 g) catalyst described above. The reaction mixture was allowed to stir for 0.5 hour after the addition of the solution of ethyl diazoacetate, CH2Cl2 and styrene. Analysis by gas chromatography showed that the combined yield of cis- and trans-ethyl-2-phenylcyclopropanecarboxylates was 95%.

Sources & evidence

ORD record
ord-bb2afe9230064bc1a80c9c13c0ac85ec
Source dataset
uspto-grants-1987_11
Patent number
US04709085

Reaction notes

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