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TCI Practical Example: Olefin Metathesis with AquaMet

We are proud to present the cyclopentene ring formation via olefin metathesis using AquaMet as a catalyst.

Used Chemicals

• Diethyl Diallylmalonate [D1183]
• AquaMet [A3009]
• Dichloromethane

Procedure

In a 200 mL two necked round bottomed flask, AquaMet (50 mg, 52 μmol) was added, and purged with N₂. Dichloromethane (100 mL) was charged in the flask, and diethyl diallylmalonate (500 mg, 2.08 mmol) in dichloromethane (20 mL) was added dropwise and the mixture was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (hexane : EtOAc = 1 : 1) to give diethyl cyclopent-3-ene-1,1-dicarboxylate as a pale yellow oil (430 mg, 98%).

Experimenter's Comments

The reaction mixture was monitored by NMR.

Analytical Data

Diethyl cyclopent-3-ene-1,1-dicarboxylate

¹H NMR (400 MHz, CDCl₃); δ 5.61 (s, 2H), 4.20 (q, J = 8.0 Hz, 4H), 3.01 (s, 4H), 1.25 (t, J = 8.0 Hz, 6H).

Lead Reference

• Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes:  Enhancement of Catalyst Activity through Electronic Activation
  • A. Michrowska, R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, K. Grela, J. Am. Chem. Soc. 2004, 126, 9318.