Vinyl propanoate → 3-Cyanocyclohex-3-en-1-yl propanoate

Participants

Reaction Steps

To a 2 L flask containing racemic 5-hydroxycyclohex-1-ene-1-carbonitrile (151 g, 1.22 mol), vinyl propionate (147 g, 1.47 mol), and MTBE (1.5 L) was added the enzyme AMANO Lipase PS from Burlholderiacepacia (20 g, Sigma-Aldrich). The mixture was stirred at ambient temperature for 48 hours. The mixture was filtered through celite and rinsed with MTBE. The filtrate was concentrated in vacuo to remove both solvent and unreacted vinyl propionate. The residue was diluted with brine (1.5 L) and extracted with hexanes (1000 mL+600 mL×3 respectively). The combined organics was washed with H2O (400 mL×5), then dried over anhydrous Na2SO4, and concentrated in vacuo to afford the title compound, which was used without further purification.

Provenance & Evidence