反応 #410347

反応方程式

(4-carboxybutyl)triphenylphosphonium bromide

potassium t-butoxide

4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-formylphenyl)benzamide

→

4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxypenten-1-yl)phenyl]benzamide

収率 67.7%

溶媒

N,N-dimethylacetamide

ethyl acetate

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred in an ice bath for 3 hours
2. 2
   洗浄the solution was washed successively with 1N hydrochloric acid (30 ml), water (20 ml) and brine (20 ml)
3. 3
   乾燥The organic phase was dried over magnesium sulfate
4. 4
   その他the solvent was evaporated in vacuo
5. 5
   その他to give an oil
6. 6
   その他The crude oil was purified by silica gel column (1% methanol in chloroform)

実験手順

To an ice bath cooled solution of (4-carboxybutyl)triphenylphosphonium bromide (371 mg) in N,N-dimethylacetamide (15 ml) was added potassium t-butoxide (188 mg) and the mixture was stirred at the same temperature for 30 minutes. To the resulting mixture was added 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-formylphenyl)benzamide (250 mg) and the mixture was stirred in an ice bath for 3 hours. The mixture was diluted with ethyl acetate (40 ml) and the solution was washed successively with 1N hydrochloric acid (30 ml), water (20 ml) and brine (20 ml). The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The crude oil was purified by silica gel column (1% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-carboxypenten-1-yl)phenyl]benzamide (201 mg) as a colorless amorphous.

出典