Reacción #61708

Ecuación de reacción

3-chloro-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzaldehyde

n-butyl lithium

→

title compound

2-Chloro-4-ethenylphenol

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to −78° C.
2. 2
   workup.WAITto reach room temperature overnight
3. 3
   Otroquenched with saturated aqueous ammonium chloride
4. 4
   ExtracciónThe resultant mixture was extracted with diethyl ether
5. 5
   Concentraciónthe combined organic extracts were concentrated under reduced pressure
6. 6
   OtroThe residue was purified
7. 7
   LavadoSPE (silica, eluting with cyclohexane, followed by 5% to 25% ethyl acetate:cyclohexane)

Procedimiento

To a slurry of methyltriphenylphosphonium bromide (0.23 g) in dry THF (5 ml) under nitrogen at −78° C., n-butyl lithium (1.6M in hexanes, 0.37 ml) was added dropwise over 2 min. The mixture was allowed to warm to 0° C., stirred for 20 min, cooled to −78° C. and a solution of 3-chloro-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzaldehyde* (0.134 g) in dry THF (5 ml) added. The reaction mixture was allowed to reach room temperature overnight and quenched with saturated aqueous ammonium chloride. The resultant mixture was extracted with diethyl ether and the combined organic extracts were concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with cyclohexane, followed by 5% to 25% ethyl acetate:cyclohexane) to give the title compound (0.049 g) as an oil. *Boukouvalas, J; Maltais, F; Lachance, N., Tetrahedron Lett. (1994), 35(43), 7897-900.

Fuente