Styrene → Ethyl 2-phenylcyclopropane-1-carboxylate

HRID 247735Notes

Reaction equation

HRID 247735 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>C(Cl)Cl>[C:3]1([CH:2]2[CH2:1][CH:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7501Styrene2×HCID 12192Ethyl diazoacetate2×

Product 1

HCID 316914Ethyl 2-phenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of CH2Cl2 (12.5 mL), styrene (12 5 mL) and ethyl diazoacetate (0.25 g, 2.19 mmol) was added slowly dropwise at ambient temperature to a stirred slurry of Rh-PFIEP[SO3H] (1.0 g, 0.387 mmol, prepared as described above), styrene (2.5 mL) and CH2Cl2 (2.5 mL). Gas evolution ceased about 1 hour after the addition of the ethyl diazoacetate solution was complete. The resulting slurry was stirred for 24 hours and then allowed to settle. The solution was removed, the resulting resin was washed with 3.0 mL of CH2Cl2. The solution and the wash were combined and analyzed for cyclopropane products. Yield (based on ethyl diazoacetate): 73.9%.

Workup

  1. customThe solution was removed
  2. washthe resulting resin was washed with 3.0 mL of CH2Cl2
  3. customYield (based on ethyl diazoacetate)

Sources & evidence

ORD record
ord-137bc18394124147bbbd48a0e5264ee2
Source dataset
uspto-grants-1987_11
Patent number
US04709085

Reaction notes

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