Water → HCID 22630117, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyanoacetate 47 (1.25 g, 4.71 mmol) in anhydrous DMSO (10 ml) was added sodium hydride (0.284 g, 7.09 mmol; 60% mineral oil dispersion). The mixture was stirred for 30 min at 50° C., and cooled to 20° C. To this was added allylbromide (0.86 g, 7.1 mmol) and the mixture was stirred for 3 h at room temperature, then for 30 min at 50° C. The mixture was cooled, treated with water and extracted with diethyl ether. The extract was washed with water and with brine, dried over anhydrous MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 20:1) to give 48 (0.92 g, 63.7%) as a colorless oil. 1H NMR (CDCl3, TMS): 0.98 (6H, s, 3′,5′-CH3eq); 1.11 (6H, s, 3′,5′-CH3ax); 1.00-1.85 (6H, m, ring CH); 1.31 (3H, t, 7 Hz, CH3-ethyl); 1.33 (3H, s, 1′-CH3); 2.42 and 2.86 (total 2H, both dd, 13 and 7 Hz, 3-CH2); 4.02 (2H, q, 7 Hz, OCH2); 5.05-5.37 (2H, m, ═CH2) and 5.55-6.05 ppm (1H, m, ═CH).

Provenance & Evidence