Dibromomethane → HCID 67159854, compound

Participants

Reaction Steps

Methyl lithium 1.6 M in diethyl ether (4 ml, 7 mmol) is added dropwise to 2-hexylcyclopent-2-enone (Isojasmone B11) (1 g, 6 mmol) in diethylether (4 ml) at −78° C. At 0°-5° C. dibromomethane (3×0.6 ml, 24 mmol) and tert-butyl magnesium chloride 2M in diethyl ether (3×4 ml, 24 mmol) are added. Work-up after 18 h at 25° C. (as described in example 1) and bulb-to-bulb distillation gives 0.7 g (60%) of a colorless oil (cisltrans=93:7). 1H NMR (CDCl3): δ 0.3 (m, 1H), 0.7 (m, 1H), 0.9 (t, 3H), 1.05 (m, 1H), 1.2-2 (15H), 1.3 (s, 3H) ppm. 13C-NMR (CDCl3): δ 11.0 (t), 14.0 (q), 22.6 (t), 23.4 (d), 24.7 (t), 25.15 (q), 27.5 (t), 29.9 (t), 31.2 (t), 31.8 (t), 34.3 (s), 37.9 (t), 81.05 (s). cis-configuration assigned by COSY, HMBC, HSQC, NOESY in CDCl3. MS (EI): m/z (%) 196 (M+, 2), 181 ([M-15]+, 14), 155 (24), 138 (15), 135 (27), 125 (32), 110 (34), 107 (38), 93 (92), 79 (50), 57 (14), 43 (100).

Provenance & Evidence