Sodium Iodide → HCID 10727305, compound

Participants

Reaction Steps

Sodium hydride (95%, 30.32 g, 1.2 mol) was suspended in anhydrous DMF (350 ml) in a 2 L, 3-necked flask and ethyl cyanoacetate (136 ml, 1.2 mol) was added dropwise with stirring under argon over 1 h. After a further 15 min, 3-bromo-2-methoxytetrahydrofuran (75 g, 0.41 mol) was added, followed by sodium iodide (2 g) and then the solution was heated with vigorous stirring at 140° C. for 20 h under argon. After cooling, water (200 ml) was added and the solution was concentrated on a rotary evaporator to about 300 ml. More water (200 ml) was added and the crude product was extracted into diethylether (4×500 ml). The combined extracts were dried (Na2SO4), filtered and evaporated. Distillation of the residue under reduced pressure through a Vigreaux column afforded a colourless liquid (13.28 g, 15%). The cut b. p. 90-110° C./0.4 mmHg was taken; Rf (in A), 0.45, 0.36; stains yellow with anisaldehyde/H+; δH(d6-DMSO) 5.00 (0.75 H, m, mixt. of trans-2-H), 4.89 (0.25 H, d J2.1, cis-2-H), 4.29-4.19 (2 H, 2 q, cis/trans-CH2), 4.06-3.83 (2 H, 2 m, cis/trans-5-H), 3.39 (0.75 H, s, MeO), 3.36 (0.75 H, s, MeO), 3.35 (0.75 H, s, MeO), 3.31 (0.75 H, s, MeO), 2.78-2.70 (1 H, m, cis/trans-3-H), 2.30-1.71 (2 H, 2 m, 2×cis/trans-4-H) ppm; m/z (EI) 213.1002 (M+; Calc. for C10H15NO4, 213.1023).

Provenance & Evidence