反应 #75951

反应方程式

tert-butyl(dimethyl)silyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl ether

triethylamine

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

tert-butyl(dimethyl)silyl [(2R)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-chromen-2-yl]methyl ether

收率 94.0%

溶剂

dioxane

反应条件

后处理

1. 1
   workup.ADDITIONwere added
2. 2
   其他The resulting reaction mixture
3. 3
   其他The resulting reaction mixture
4. 4
   过滤was filtered through a Celite pad
5. 5
   浓缩The filtrate was concentrated
6. 6
   其他purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes:EtOAc=10:1)
7. 7
   其他The product was obtained as a pale brown waxy solid in 94% yield
8. 8
   其他MH+=405.3, retention time (LC-MS) =4.79 min.

实验过程

Argon was bubbled through a solution of tert-butyl(dimethyl)silyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl ether (Example 59, 11.1 mmol, 1.0 eq.) in dioxane (45 mL) for 10 minutes before Pd(dppf)Cl2 (0.306 mmol, 0.03 eq.), triethylamine (33.4 mmol, 3.0 eq.), and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (17.8 mmol, 1.6 eq.) were added. The resulting reaction mixture was stirred at 80° C. overnight. The resulting reaction mixture was filtered through a Celite pad. The filtrate was concentrated and purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes:EtOAc=10:1). The product was obtained as a pale brown waxy solid in 94% yield. MH+=405.3, retention time (LC-MS) =4.79 min.

来源