methyl (E)-non-2-enoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared as described in Example 23 from methyl lithium 1.6 M in diethyl ether (7.4 ml, 12 mmol) and (E)-methyl non-2-enoate (Neofolione) (1 g, 6 mmol) in diethyl ether (10 ml) at −78° C., followed by dibromomethane (5×1 g, 30 mmol) and tert-butyl magnesium chloride 2M in diethyl ether (5×3 ml, 30 mmol) at 0°-5° C. Work-up after 18 h at 25° C. and bulb-to-bulb distillation under high vacuum gives 0.8 g (74%) of a colorless oil. 1H NMR (CDCl3): δ 0.15 (m, 1H), 0.45 (m, 1H), 0.7 (2 m, 2H), 1.15 (s, 3H), 1.2 (s, 3H), 1.2-1.4 (7H) ppm. 13C-NMR (CDCl3): δ 8.1 (t), 14.1 (q), 15.1 (d), 22.6 (t), 28.4 (q), 28.9 (q), 29.2 (t), 29.4 (t), 30.3 (d), 31.9 (t), 34.1 (t), 69.7 (s). MS (EI): m/z (%) 169 ([M-15]+, 19), 151 (3), 123 (4), 110 (11), 109 (12), 97 (14), 95 (37), 72 (88), 71 (89), 43 (100). IR (film): 3377 (br, OH), 2960 (m), 2922 (s), 2853 (m), 1464 (m), 1367 (m), 1229 (w), 1145 (m), 944 (m), 915 (m). Prepared bulb-to-bulb distillation under high vacuum