反応 #7390

反応方程式

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

n-butyl lithium

→

title compound

2-Chloro-4-ethenylphenol

溶媒

THF

THF

反応条件

後処理

1. 1
   温度cooled to −78° C.
2. 2
   workup.WAITto reach room temperature overnight
3. 3
   その他quenched with saturated aqueous ammonium chloride
4. 4
   抽出The resultant mixture was extracted with diethyl ether
5. 5
   濃縮the combined organic extracts were concentrated under reduced pressure
6. 6
   その他The residue was purified
7. 7
   洗浄SPE (silica, eluting with cyclohexane, followed by 5% to 25% ethyl acetate:cyclohexane)

実験手順

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.

出典