[CH3:1][CH:2]1[CH:9]2[CH2:10][CH:5]([C:6]([CH3:11])=[CH:7][CH2:8]2)[CH:4]([OH:12])[CH2:3]1.[Na].[CH3:14]I>O1CCCC1>[CH3:14][O:12][CH:4]1[CH2:3][CH:2]([CH3:1])[CH:9]2[CH2:10][CH:5]1[C:6]([CH3:11])=[CH:7][CH2:8]2To a solution of 10 g (60.2 mmol) of 4,8-dimethylbicyclo[3.3.1]nona-7-en-2-ol [IA] in 60 ml of tetrahydrofuran were added 1.3 g (56.5 mmol) of sodium and the resulting mixture was heated with stirring at 40° C. After the sodium was dissolved, 12.8 g (90 mmol) of methyl iodide were added dropwise and the resulting mixture was heated with stirring at 40° C. for 10 hours. After cooling, the tetrahydrofuran was distilled off under reduced pressure, the residue was subjected to column chromatography and eluate with toluene gave 7.8 g of the title compound, which had a refrigerant and camphor-like smell.
불러오는 중…
