反応 #93585

反応方程式

n-butyllithium

hexane

diisopropylamine

3-(3,4-dimethoxyphenyl)propionic acid

2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-iodopropyl)acetonitrile

2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile

HCl

→

1-(3,4-dimethoxyphenyl)-2-carboxy-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane

収率 91.7%

溶媒

Hexamethylphosphoramide

THF

THF

water

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度cooled to -50° C
3. 3
   温度to warm to room temperature
4. 4
   workup.STIRRINGwhile stirring for 12 hours
5. 5
   抽出extracted three times with ether
6. 6
   洗浄The organic layer was washed with aqueous Na2SO3 and brine
7. 7
   乾燥dried over Na2SO4
8. 8
   その他evaporated

実験手順

A 1.6M solution of n-butyllithium in hexane (91.8 mL, 147 mmol) was added to a -20° C. solution of diisopropylamine (21 mL, 150 mmol) in THF (480 mL). Hexamethylphosphoramide (56 mL) was added and the mixture maintained at -20° C. while a solution of 3-(3,4-dimethoxyphenyl)propionic acid (15.1 g, 72 mmol) in THF (75 mL) was added. The resulting solution was stirred at room temperature for one hour, and then cooled to -50° C. A solution of 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-iodopropyl)acetonitrile (22, 27.9 g, 72 mmol) was added, and the mixture allowed to warm to room temperature while stirring for 12 hours. The resulting mixture was added to water, acidified with HCl, and extracted three times with ether. The organic layer was washed with aqueous Na2SO3 and brine, dried over Na2SO4, and evaporated to yield 1-(3,4-dimethoxyphenyl)-2-carboxy-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (23, 31 g) as a thick oil.

出典