Reaction Steps
Prepared as described in Example 24 from 1-vinyl-9-oxabicyclo[6.1.0]nonane (J P Kokai S49-047345, Takasago Perfumery Co., Ltd.) (3 g, 18 mmol), n-butyl lithium 1.6 M in hexane (11 ml, 18 mmol), dibromomethane (12.5 g, 72 mmol) and tent-butyl magnesium chloride (36 ml, 72 mmol). Work-up and bulb-to-bulb distillation at 98° C./0.05 mbar gave 2.6 g (65%) of a colorless oil (dr=93:7). 1H NMR (CDCl3): δ 0.3 (m, 1H), 0.5 (m, 1H), 0.8 (m, 1H), 0.8-1.1 and 1.2-2.4 (22H), 3.25 (1H) ppm. 13C-NMR (CDCl3): δ 14.1 (q), 20.7 (t), 22.7 (t), 23.3 (t), 23.5 (t), 24.3 (d), 26.5 (t), 26.8 (t), 28.9 (t), 29.4 (s), 29.7 (t), 30.4 (t), 31.2 (t), 31.7 (t), 73.7 (d). cis-configuration assigned by COSY, HMBC, HSQC, NOESY in DMSO-D6. MS (EI): m/z (%) 224 (M+, 1), 206 ([M-18]+, 10), 178 (4), 163 (5), 149 (12), 135 (22), 126 (24), 109 (22), 107 (24), 98 (58), 97 (33), 96 (80), 95 (46), 93 (54), 69 (41), 68 (42), 67 (84), 55 (100), 41 (80). IR (film): 3362 (br, OH), 2919 (s), 2852 (m), 1456 (m), 1364 (w), 1106 (w), 1029 (m), 989 (m), 811 (w), 741 (w), 726 (w).
