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TCI Practical Example: Cross Metathesis Using UltraNitroCat
We are proud to introduce the cross metathesis using UltraNitroCat as a catalyst.
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Used Chemicals
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Procedure
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To a solution of ethyl 10-undecenoate (0.400 mL, 1.7 mmol), acrylonitrile (0.210 mL, 3.2 mmol) in anhydrous toluene (5.8 mL) at 70 °C under nitrogen, a solution of UltraNitroCat (3.4 mg, 0.005 mmol, 0.3 mol%) in toluene (0.5 mL) was dropwised over 1 h. The mixture was stirred at 70 °C under nitrogen for 3 hours. 1,4-Bis(3-isocyanopropyl)piperazine (0.5 mol%, 5.0 mg) was added to the reaction mixture to deactivate the catalyst. The solvent was removed under reduced pressure to obtain a light yellow oil (0.37 g).
The crude oil was analyzed by gas chromatography. The reaction conversion rate of 1 and 2 were 69.3% and 6.3%, respectively. The selectivity ratio of 1 and 2 was 92 : 8.
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Experimenter's Comments
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Toluene was dried over molecular sieves 4A and degassed by purging with nitrogen before use.
Preparation of catalyst stock solution: UltraNitroCat (6.9 mg) was dissolved in dry degassed toluene (1.0 mL).
The reaction mixture was analyzed by GC.
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Analytical Data
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1: 11-Cyano-10-undecenoic acid ethyl ester
1H NMR (400 MHz, CDCl3); δ 6.47 (m, 1H), 5.30 (m, 1H), 4.12 (m, 2H), 2.41 (m, 2H), 2.03 (m, 2H), 1.61 (m, 2H), 1.43 (m, 2H), 1.22 (m, 11H).
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2: 10-Eicosenedioic acid diethyl ester
1H NMR (400 MHz, CDCl3); δ 6.71 (m, 2H), 5.36 (m, 2H), 4.12 (m, 4H), 2.21 (m, 4H), 1.96 (m, 4H), 1.61 (m, 4H), 1.43 (m, 4H), 1.22 (m, 22H).
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Lead Reference
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- Cyclic Alkyl Amino Ruthenium Complexes—Efficient Catalysts for Macrocyclization and Acrylonitrile Cross Metathesis
