Reacción #7391

Ecuación de reacción

4-chloro-3-hydroxy-benzaldehyde

tert-butyldimethylsilyl chloride

triethylamine

→

title compound

3-{[tert-Butyl(dimethyl)silyl]oxy}-4-chlorobenzaldehyde

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was quenched with saturated aqueous sodium bicarbonate
2. 2
   Extracciónextracted with diethyl ether
3. 3
   ConcentraciónThe combined organic extracts were concentrated under reduced pressure
4. 4
   Otroto give an oil which
5. 5
   Otrowas purified
6. 6
   LavadoSPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate-cyclohexane)

Procedimiento

A mixture of 4-chloro-3-hydroxy-benzaldehyde* (0.354 g), 4-N,N-dimethylaminopyridine (0.028 g), tert-butyldimethylsilyl chloride (0.409 g) and triethylamine (0.473 ml) in DCM (15 ml) was stirred at room temperature under nitrogen for 19 h. The mixture was quenched with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The combined organic extracts were concentrated under reduced pressure to give an oil which was purified using SPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate-cyclohexane) to give the title compound (0.42 g) as an oil. *Kelley, J; Linn, J; Selway, J. W. T., J. Med. Chem. (1989), 32(8), 1757–63.

Fuente