C([Mg])=C.ClC1CCCCCCCCCCC1=O.Cl.[OH-].[Na+].[CH:21]([C@@:23]12[O:35][C@@H:34]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH2:22]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.O1CCCC1>[CH:21]([C@@:23]12[O:35][C@H:34]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH2:22]
A four-neck flask equipped with a thermometer, stirrer and condenser tube was charged with a tetrahydrofuran solution of vinylmagnesium (1.31 mol), and toluene (600 ml) was added to the solution. At 0° C., a toluene solution of 2-chlorocyclododecanone (159 g, 0.735 mol) was added dropwise to the solution, for reaction for 1 hour. After completion of reaction, 16% hydrochloric acid (120 g) was added for hydrolysis, and the solution was separated to take out the organic layer. The organic layer was washed with 2% sodium hydroxide aqueous solution (320 ml). To the obtained toluene solution, added were 30% sodium hydroxide aqueous solution (370 g, 2.78 mol) and benzyltriethylammonium chloride (1.86 g 0.00816 mol), and the mixture was stirred for reaction at 95° C. for 6 hours. After completion of reaction, the solution was separated to take out the organic layer, and the organic layer was washed with a saline solution. The solvent was distilled away under reduced pressure, and the residue was distilled for purification under reduced pressure, to obtain 133 g of a distillate. It was analyzed by means of capillary gas chromatography and found to be a mixture containing 61% of cis-1-vinyl-13-oxabicyclo[10.1.0]tridecane and 37% of trans-1-vinyl-13-oxabicyclo[10.1.0]tridecane (yield was 85%). The distillate was partially separated by means of silica gel chromatography for isolation into trans-1-vinyl-13-oxabicyclo[10.1.0]tridecane and cis-1-vinyl-13-oxabicyclo[10.1.0]tridecane.
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