[Li]CCCC.CCCCCC.C(#N)C.[CH:15]12[CH2:24]C3CC(CC(C3)[C:16]1=[O:25])[CH2:22]2.[C:26]([CH2:28][C:29]1([OH:39])[CH:36]2[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:38][CH:30]1[CH2:31]3)[CH2:35]2)#[N:27].C(OC(=O)C(C)=C)(=O)C(C)=C.C(N(CC)CC)C>O1CCCC1.CCCCCC.C(OCC)C.O>[C:16]([O:39][C:29]1([CH2:28][C:26]#[N:27])[CH:30]2[CH2:38][CH:34]3[CH2:33][CH:32]([CH2:37][CH:36]1[CH2:35]3)[CH2:31]2)(=[O:25])[C:15]([CH3:24])=[CH2:22]A glass reactor of 500 ml which was equipped with a stirrer and dropping funnel was charged with 100 ml of dried tetrahydrofuran, and it was cooled (−78° C.) on a dry ice/isopropanol bath and then charged with 100 ml (160 millimole) of a n-BuLi/n-hexane solution (1.6M). Acetonitrile 10 ml (192 millimole) was dropwise added thereto in 10 minutes. The solution stayed in a slurry state by a deposit. A solution obtained by dissolving 22.2 g (148 millimole) of adamantanone (Adamantanone, manufactured by Idemitsu Petrochemical Co., Ltd.) in 100 ml of tetrahydrofuran was dropwise added thereto. The deposit was slowly dissolved, and the solution became transparent. After finishing dropwise adding, the temperature was slowly elevated up to 0° C., and gas chromatographic analysis was carried out to confirm that adamantanone was completely converted to Li alkoxide of 2-cyanomethyl-2-adamantanol at a selectivity of 99.5%. This reaction liquid was dropwise added in 30 minutes to a solution of 47 ml (318 millimole) of methacrylic anhydride, 45 ml (320 millimole) of dried triethylamine and 100 ml of dried tetrahydrofuran while the solution was cooled to 0° C. on an ice and water bath. After further stirred at 0° C. for 30 minutes, 200 mol of water and 300 ml of diethyl ether were added thereto and stirred. This solution was transferred into a separating funnel of 2 liter to remove an aqueous phase, and then an organic phase was washed with diluted hydrochloric acid to remove a Li salt and a triethylamine salt. Further, this was neutralized by a sodium carbonate aqueous solution and then washed with water. The organic phase was dried on anhydrous magnesium sulfate, and then the solvent was distilled off by means of an evaporator to obtain 38 g of a crude reaction product. n-Hexane 100 ml was added to the crude reaction product, and the solution was cooled while stirring to remove deposited 2-cyanomethyl-2-adamantanol by filtration. Activated carbon was added to the n-hexane solution to confirm that the solution became colorless, and it was filtered off. Then, the solvent was distilled off by means of an evaporator to obtain a colorless liquid. It was analyzed by gas chromatography to confirm that the intended product having a purity of 97.0% was obtained at a yield of 35.0 g. The respective data of 1H-NMR, 13C-NMR and GC-MS are shown below.
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