Reacción #7813

Ecuación de reacción

EtOAc

NaH

5-(1,3-benzoxazol-2-yl)-2-methylphenol

(2-bromoethoxy)(tert-butyl)dimethylsilane

→

2-[3-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethoxy)-4-methylphenyl]-1,3-benzoxazole

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITThe reaction was then elevated to 90° C. for 1 h
2. 2
   LavadoThe EtOAc solution was washed with brine (3×20 mL)
3. 3
   Secadodried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by flash column (silica gel, hexanes:EtOAc 1:5)

Procedimiento

A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (355 mg, 1.6 mmol) in DMF (10 mL) was cooled to 0° C. and NaH (70 mg, 1.7 mmol) was added slowly. After 15 min, (2-bromoethoxy)(tert-butyl)dimethylsilane (370 μL, 1.7 mmol) was added. The reaction was then elevated to 90° C. for 1 h and EtOAc (100 mL) was added. The EtOAc solution was washed with brine (3×20 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash column (silica gel, hexanes:EtOAc 1:5) to afford 2-[3-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethoxy)-4-methylphenyl]-1,3-benzoxazole.

Fuente