(E)-2-CYANO-5-METHYL-HEX-2-ENOIC ACID METHYL ESTER synthesis

Yield:96914-67-9 100 g (60%)

Reaction Conditions:

with ammonium acetate in acetic acid;ethyl acetate;benzene;

Steps:

15.F F.

F. 2-Cyano-5 methyl-hex-2-enoic acid methyl ester To a solution of isovaleraldehyde (86.1 g, 1 mol) in dry benzene (100 mL) was added methyl cyanoacetate 2 (99.1 g, 1 mol), ammonium acetate (10 g) and glacial acetic acid (20 mL). The reaction mixture was stirred at 0° C. for 1 hour and allowed to cool to room temperature. Excess of solvents was removed in vacuo and the residue was dissolved in EtOAc (400 mL). The organic layer was washed with water, dried over sodium sulfate and evaporated to give the product as pale yellow oil. Further purification of the pale yellow oil by distillation (10 mm Hg) gave 100 g (60%) of 2-cyano-5 methyl-hex-2-enoic acid methyl ester as a colorless oil: ¹H NMR (300 MHz, CDCl₃) δ 1.00 (d, J=6.7 Hz, 6H), 1.91 (m, 1H), 2.47 (dd, J=7.9, 6.8 Hz, 2H), 3.89 (s, 3H), 7.69 (t, J=8.0 Hz, 1H).

References:

US2004/147608,2004,A1