反应详情

The catalyst [(10% Pd/C, 5.0 mg, 0.12 mol %), (Tris(triphenylphosphine)rhodium(I) chloride, 0.05 g, 1.35 mol %) (bis(norbornadiene)rhodium(I) BF4, Taniaphos, 0.003 mmol, 0.75 mol %)] was weighed into a dry 2-neck round bottom flask. The predried CIL (2.0 mL) was then added to the flask, followed by dimethyl itaconate 5 (0.63 g, 4.00 mmol) and 3 N2/vacuum cycles were performed. The reaction mixture was stirred for 10 minutes or until reaching 55° C. Hydrogen was then introduced to the reaction via a balloon, and the progress of the reaction was monitored by 1H NMR. Upon termination of the reaction, the products were extracted using hexane (10×3 mL). The mass recovery after extraction from the CIL was 100% (0.63 g). Dimethyl 2-methylsuccinate 9 was obtained in 98% yield (0.63 g, 3.94 mmol) as a racemic mixture using either Pd—C (KG 813) or Wilkinson's catalyst (KG 834) and in 68% conversion using the Taniaphos catalyst (KG 813).

1. additionThe predried CIL (2.0 mL) was then added to the flask
2. customuntil reaching 55° C
3. customUpon termination of the reaction
4. extractionthe products were extracted
5. extractionThe mass recovery after extraction from the CIL