反应详情

温度

0 °C

Freshly prepared methylmagnesium iodide in ether (1 M, 85 mL), was added through a canola to 5-phenyladamantan-2-one (9.6 g, 42.5 mmol) obtained in step II, in THF (85 mL) at 0° C. After stirring at 0° C. for 0.5 h, the reaction mixture was quenched by adding sat. aq. NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with diisopropylether. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure to obtain 2-methyl-5-phenyl-adamantan-2-ol (9.9 g) as an off-white solid in 97% yield. M.R: 98-100.4° C. m/z (M+23) 265; 1H NMR (CDCl3) 300 MHz δ 7.42-7.28 (m, 4H), 7.24-7.18 (m, 1H), 2.47-2.26 (m, 2H), 2.14-2.09 (m, 3H), 1.96-1.70 (m, 6H), 1.61-1.57 (m, 2H), 1.42 (s, 3H). 13C NMR (CDCl3) 75 MHz δ 150.0, 128.1 (2C), 125.7, 124.8 (2C), 73.3, 44.0 (2C), 40.5 (2C), 39.6 (2C), 35.9, 32.0, 27.6.

1. customthe reaction mixture was quenched
2. additionby adding sat. aq. NH4Cl solution
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with diisopropylether
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried over anhydrous Na2SO4
7. customthe solvent was removed under reduced pressure