반응 #7390

반응 방정식

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

n-butyl lithium

→

title compound

2-Chloro-4-ethenylphenol

용매

THF

THF

반응 조건

후처리

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

실험 절차

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.

출처