Reacción #85809

Ecuación de reacción

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

sodium hydride

CH3I

→

title compound

tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 0° C
2. 2
   Temperaturacooled to 0° C
3. 3
   workup.ADDITIONAfter the completion of the addition
4. 4
   workup.STIRRINGthe reaction mixture was stirred at room temperature overnight
5. 5
   Otroquenched with H2O
6. 6
   Extracciónextracted with EtOAc
7. 7
   ConcentraciónThe combined extracts were concentrated
8. 8
   Otrothe residue was purified by flash chromatography

Procedimiento

Under N2, to a solution of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (500 mg, 1.57 mmol) in anhydrous THF (4 mL), was slowly added sodium hydride (94 mg, 2.35 mmol) at 0° C. The mixture was stirred at room temperature for 20 minutes, then cooled to 0° C. CH3I (445 mg, 3.13 mmol) was slowly added. After the completion of the addition, the reaction mixture was stirred at room temperature overnight, quenched with H2O, and extracted with EtOAc. The combined extracts were concentrated, and the residue was purified by flash chromatography to give the title compound. MS (m/z): 278 (M−56)+.

Fuente