Dimethyl malonate → HCID 11482150, compound

Participants

Reaction Steps

A mixture of (Z)-2-(2-pentenyl)-2-cyclopenten-1-ol (17.8 g; 117 mmol), dimethyl malonate (17.8 g; 135 mmol), ground KHCO3 (0.58 g; 5.8 mmol) and Novozym 435® (immobilized Candida antarctica from Novo Nordisk; 1.80 g) was gently swirled in a 100 ml flask connected to a Büchi rotavapor at 40° C. and 10 hPa. After 80 min., the reaction mixture was filtered, washed (sat. aq. NaHCO3, sat. aq. NaCl), dried (Na2SO4) and concentrated (30.8 g). Bulb-to-bulb distillation afforded 15.5 g of volatiles (oven temp. 70° C./10-0.1 hPa) and ca. 11.14 g (95% pure, 36%, 97% ee) of the desired product which is isolated at an oven temperature of 80-130° C./0.06 hPa.

Provenance & Evidence