反应 #1519149

反应方程式

1-tetralone

n-butyllithium

4-bromopyridine

ammonium chloride

→

expected product

1-(4-Pyridyl)-1,2,3,4-tetrahydro-1-naphthol

溶剂

ether

hexane

ether

反应条件

后处理

1. 1
   workup.ADDITIONat the end of the addition
2. 2
   其他to return to ambient temperature
3. 3
   workup.STIRRINGAfter stirring overnight
4. 4
   其他After separation, extraction with ether
5. 5
   萃取extracted with 1N hydrochloric acid
6. 6
   萃取extracted with dichloromethane
7. 7
   其他After drying

实验过程

85 ml of a 1.5M solution of n-butyllithium in hexane are added, dropwise, to a solution of 20 g of 4-bromopyridine in 73 ml of ether, cooled to −78° C. Stirring is carried out for 30 minutes at that temperature, a solution of 1-tetralone in 73 ml of ether is then poured in and, at the end of the addition, the mixture is allowed to return to ambient temperature. After stirring overnight, a saturated aqueous solution of ammonium chloride is poured in. After separation, extraction with ether is carried out. The ethereal phases are combined and extracted with 1N hydrochloric acid. The combined acid phases are adjusted to pH=8 using 20% sodium hydroxide solution and extracted with dichloromethane. After drying, the expected product is isolated, which is purified by high-speed chromatography on silica (eluant: dichloromethane/methanol 95/5) to yield the expected product.

来源