تفاعل #54061

معادلة التفاعل

water

sodium bis(trimethylsilyl)amide

crotyl bromide

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

→

4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

المردود 73.2%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with EtOAc three times
2. 2
   غسيلwashed sequentially with saturated aqueous sodium bicarbonate solution, water, and brine
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was purified by flash chromatography

الإجراء التجريبي

A mixture of 70 mg of 4-(1-hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester in 2 mL of DMSO was treated with 0.22 mL of 1.0 M sodium bis(trimethylsilyl)amide and 29 mg of crotyl bromide at room temperature. The reaction mixture was allowed to stir at room temperature overnight. The reaction was worked up by adding water and extracted with EtOAc three times. The organic layers were combined, washed sequentially with saturated aqueous sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to yield 58 mg of 4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid.

المصدر