[CH:1]([Mg])=[CH2:2].Cl[CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:17].Cl.[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O1CCCC1>[CH:1]([C:7]12[O:17][CH:6]1[CH2:5][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH2:2]
A four-neck flask equipped with a thermometer, stirrer and condenser tube was charged with a tetrahydrofuran solution of vinylmagnesium (24 mmol), and toluene (16 ml) was added to the solution. At 0° C., a toluene solution of 2-chlorocyclododecanone (2.93 g, 13.5 mmol) was added dropwise for reaction for 1 hour. After completion of reaction, 16% hydrochloric acid (5 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 (10 ml). To the obtained toluene solution, added were 30% sodium hydroxide aqueous solution (6.8 g, 51.0 mmol) and tetrabutylammonium chloride (0.0417 g, 0.150 mmol), and the mixture was stirred for reaction at 95° C. for 2 hours. After completion of reaction, the solution was separated to take out the organic layer, and the organic layer was washed with 10% sulfuric acid (5 ml), saturated sodium hydrogencarbonate aqueous solution (10 ml) and a saline solution (10 ml). The solvent was distilled away under reduced pressure, and the residue was distilled for purification under reduced pressure, to obtain 1-vinyl-13-oxabicyclo[10.1.0]tridecane (2.44 g, 11.5 mmol, chemical purity 98%, cis form:trans form=59:41). The yield was 85%.
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