反応 #2552

反応方程式

o-anisidine

triethylamine

sodium hydroxide

4-chloromethylbenzoyl chloride

2-bromomethyl-1,3-dioxolan

→

title compound

収率 47.9%

4-Chloromethyl-N-(2-methoxyphenyl)-N-(1,3-dioxolan-2-yl)methylbenzamide

収率 47.9%

溶媒

methylene chloride

反応条件

後処理

1. 1
   温度with cooling in an ice bath
2. 2
   workup.STIRRINGAfter 1 hour of stirring at the same temperature
3. 3
   抽出the resulting mixture was extracted with methylene chloride
4. 4
   洗浄washed with 10% citric acid aqueous solution and saturated brine
5. 5
   乾燥dried on anhydrous sodium sulfate
6. 6
   その他Thereafter, the solvent was removed by evaporation
7. 7
   その他the resulting residue was purified

実験手順

In an atmosphere of argon, a mixture consisting of o-anisidine (500 mg, 4.06 mmol), triethylamine (1.6 ml, 11.5 mmol) and 2-bromomethyl-1,3-dioxolan (0.96 ml, 8.18 mmol) was stirred at 80° C. for 4 days, dissolved in methylene chloride (8 ml) and then, with cooling in an ice bath, mixed with 20% sodium hydroxide aqueous solution (4 ml) and 4-chloromethylbenzoyl chloride (768 mg, 4.06 mmol). After 1 hour of stirring at the same temperature, the resulting mixture was extracted with methylene chloride, washed with 10% citric acid aqueous solution and saturated brine and then dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ethyl acetate:hexane=2:5) to obtain 704 mg (47.9%) of the title compound in the form of colorless solid.

出典