反応 #59837

反応方程式

sodium carbonate

2-formyl-4-isopropylphenyl trifluoromethanesulfonate

6-isopropylnaphthalene-2-boronic acid

→

aimed compound

収率 70.0%

5-isopropyl-2-(6-isopropyl-2-naphthyl)benzaldehyde

収率 70.0%

溶媒

dimethoxyethane

反応条件

後処理

1. 1
   その他equipped with a cooling pipe
2. 2
   温度under heating for 8 hours
3. 3
   その他After the reaction terminated
4. 4
   workup.ADDITIONadding water in an amount of 100 milliliter into the reacted solution
5. 5
   その他an organic layer was separated
6. 6
   洗浄washed with the use of sodium chloride solution
7. 7
   乾燥by drying with the use of magnesium sulfate
8. 8
   その他After removing the solvent
9. 9
   workup.DISTILLATIONby distillation
10. 10
    その他by means of a rotary evaporator

実験手順

Under an atmospheric argon gas flow, 2-hydroxy-5-isopropylbenzaldehyde in an amount of 4.4 g (27 mmol), trifluoromethane sulfonic acid anhydride in an amount of 11.2 g (40 mmol), pyridine in an amount of 6 milliliter (80 mmol) and dichloromethane in an amount of 100 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred at the room temperature for 2 hours. After the reaction terminated, the resultant was separated by filtration, and after washing the resultant crude product with the use of hexane and dichloromethane, the resultant solution was vacuum dried at a temperature of 50° C. for 8 hours and as a result, 6.0 g of 2-formyl-4-isopropylphenyltrifluoromethanesulfonate (white crystal) was obtained (yield: 75%). Subsequently, under an atmospheric argon gas flow, 2-formyl-4-isopropylphenyl trifluoromethanesulfonate in an amount of 5.9 g (20 mmol), 6-isopropylnaphthalene-2-boronic acid in an amount of 4.7 g (22 mmol), (tetrakistriphenylphosphine)palladium in an amount of 1.1 g (1 mmol), 2N sodium carbonate aqueous solution in an amount of 30 milliliter and dimethoxyethane in an amount of 40 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was refluxed under heating for 8 hours. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=60/40), and as a result, 4.4 g of an aimed compound (white crystal) was obtained (yield: 70%).

出典