Carbon Dioxide → HCID 70167656, compound

Participants

Reaction Steps

Dimethyl (S)-(−) malate (0.27 mL, 2 mmol) is dissolved in anhydrous N,N-dimethylforamide (8 mL), and powdered cesium carbonate (1.95 g, 6 mmol, 3 eq) is added. The suspension is then stirred at room temperature while passing carbon dioxide gas for 1 hour before benzyl chloride (0.69 mL, 6 mmol, 3 eq) is added to the solution. Carbon dioxide gas is continuously bubbled through the solution for another 2˜3 hours until the starting material is consumed. The reaction is quenched with water (20 mL) and extracted with EtOAc (3×20 mL). The resulting organic layer is washed consecutively with water (3×20 mL), brine (20 mL), and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo provides an oil, which is purified by column chromatography (9:1 Hexanes-EtOAc) to yield 384 mg of the desired dimethyl malate benzyl carbonate (65%): IR (thin film) 3034, 2957, 1746, 1439, 1383, 1216, 1042, 909, 756, 699 cm−1; 1H NMR (360 MHz, CDCl3) d 2.93 (d, 2H, J=6.26 Hz), 3.71 (s, 3H), 3.78 (s, 3H), 5.22 (s, 2H, J=6.08 Hz), 7.34-7.38 (m, 5H); 13C NMR (90 MHz, CDCl3) d 35.60, 51.97, 52.55, 70.00, 71.13, 128.17, 128.43, 153.94, 168.80, 169.10.

Provenance & Evidence