[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([Li])CCC.[CH2:11]([Li])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CCCCCC>[CH3:6][C:2](=[CH:3][CH2:4][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:1][OH:5]A hexane solution of n-butanol (77.1 mg; 1.0 mmol) was cooled to 0° C. under an argon atmosphere, and a hexane solution of n-butyllithium (1.0 ml) was added dropwise thereto and stirred. To the resulting solution, there was further dropwise added a hexane solution of n-octyllithium (1.2 mmol) and a hexane solution of 3-methyl-3,4-epoxybutene-1 (88.1 mg; 1.0 mmol), and after the addition was completed, the resulting mixture was cooled at 0° C. for 1 hour and at room temperature for 1.5 hours, followed by the usual work up. Removal of the solvent and distillation of the residue gave 150 mg of 2-methyl-2-dodecen-1-ol (yield, 75%; Z/E=93.0/7.0).
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