Water → HCID 22412559, compound

Participants

Reaction Steps

A solution of the chloride (31) (1.52 g) and sodium cyanide (0.22 g) in DMF (50 ml) was stirred at 60° C. for 3 h. It was poured into water (100ml), and extracted with ether -hexane (1:1, 150 ml ). The organic fraction was washed with water, dried (MgSO4) and the solvent evaporated to give an oil, which was crystallised from hexane (80 ml) to give (32), (1.31 g, 88%), as needles, m.p 63°-66° C., Found C. 73.0, 9.7, N 3.8, C21H33NO3 requires C 72.6, 9.6, N 4.0%!; vmax (KBr)/cm-1 3334 m, 2250 m, 1511 s, 1425 s, 1395 s, 1216 s, 1192 s, 1034 s, 998 s, 871 m, 724 m; δH (250.1 MHZ; CDCl3) 0.9-1.9 (22H, m), 4.36 (4H, m), 2.42 (1H, t, J=5), 3.68 (2H, s), 4.66 (2H, d, J=5), 6.84 (1H, s), 6.89 (1H, s); δC (62.9 MHz; CDCl3) 14.1, 18.7, 22.7, 25.9, 29.4, 31.7, 62.0, 69.1, 112.4, 112.7, 118.3, 130.2, 150.2, 150.7, m/z (CI) 347 (M+, 43), 330 (100), 263 (5).

Provenance & Evidence