反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
PROCEDURE
实验过程
To a solution of 1-[3-(tert -butyldimethylsilanyl)prop-2-ynyl]-4-(1-hydroxy-2-phenylethyl)-6-iodo-3-methyl-1H-pyridin-2-one 4a (60 mg, 0.12 mmol) and 4-dimethylaminopyridine (2 mg, 1.2 μmol) in CH2Cl2 (2 mL) was added NEt3 (49 mg, 66 μL, 0.48 mmol) and chlorodimethyloctylsilane (62 mg, 77 μL, 0.3 mmol). The resulting mixture was stirred for 12 h. The solvent was evaporated and the residue was purified by flash chromatography (hexanes-EtOAc 15:1) to afford 5a (41 mg, 51%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ7.32-7.24 (m, 3H), 7.15-7.12 (m, 2H), 7.08 (s, 1H), 5.14 (d, J=17.0, 1H), 5.09 (d, J=17.0, 1H), 4.79 (t, J=6.4 Hz, 1H), 2.79 (d, J=6.4 Hz, 2H), 1.98 (s, 3H), 1.39-1.11 (m, 14H), 0.94 (s, 9H), 0.90-0.87 (m, 3H), 0.10 (s, 6H), −0.17 (s, 3H), −0.18 (s, 3H); 13C NMR (75 MHz, CDCl3) δ162.3, 152.0, 137.8, 129.7, 129.1, 128.3, 127.5, 127.2, 126.6, 118.6, 88.4, 44.6, 33.5, 32.0, 29.4, 29.3, 26.1, 23.2, 23.0, 22.7, 17.9, 16.5, 14.2, 12.0, −0.19, −2.05, −4.78.
WORKUP
后处理
- customThe solvent was evaporated
- customthe residue was purified by flash chromatography (hexanes-EtOAc 15:1)