反応 #54071

反応方程式

sodium bis(trimethylsilyl)amide

2-bromophenethyl alcohol

4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

→

4-{1-[2-(2-bromophenyl)ethoxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

溶媒

DMSO

DMSO

反応条件

後処理

1. 1
   その他was consumed
2. 2
   その他The reaction was quenched with water
3. 3
   抽出the product was extracted with EtOAc three times
4. 4
   洗浄washed sequentially with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and brine
5. 5
   乾燥dried over magnesium sulfate
6. 6
   その他the solvent evaporated in vacuo
7. 7
   その他The residue was purified by flash chromatography

実験手順

A mixture of 0.037 mL of 2-bromophenethyl alcohol and 1 mL of DMSO was treated with 0.277 mL of 1.0 M sodium bis(trimethylsilyl)amide, then 86 mg of 4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester in 1 mL DMSO was added at room temperature. The reaction mixture was allowed to stir at room temperature overnight. TLC showed starting material was consumed. The reaction was quenched with water and the product was extracted with EtOAc three times. The organic layers were combined, washed sequentially with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, and the solvent evaporated in vacuo. The residue was purified by flash chromatography to yield 37 mg of 4-{1-[2-(2-bromophenyl)ethoxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as an oil.

出典