Sodium Cyanide → Benzyl 10-cyano-2-cyclopentyldecanoate

Participants

Reaction Steps

A mixture of the iodoester from step 2, (3.99 g, 8.7 mmol) and sodium cyanide (0.47 g, 9.6 mmol) in 15 mL of anhyd. DMSO was heated at 70°-75° C. for 30 min. After cooling, the reaction mixture was poured over ice (~ 40 g), extracted into ether and washed successively with water and saturated brine. The organic layer was concentrated to yield an oil (2.89 g). 1H NMR (300 MHz, CDCl3). δ: 7.35 (m, 5H), 5.15 (s, 2H), 2.30(t, 8 Hz, 2H), 2.20(m, 1H), 2.00(m, 1H), 1.3-1.8 (m, 22H).

Provenance & Evidence