تفاعل #1702096

معادلة التفاعل

5-(3,3-Dimethyl-but-1-ynyl)-3-[2-(ethoxy-methyl-phosphinoyl)-ethylamino]-thiophene-2-carboxylic acid methyl ester

4-methyl-cyclohexanecarbonyl chloride

→

5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester

المردود 80.5%

المذيبات

EtOAc

pyridine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe heat to the oil bath
2. 2
   workup.STIRRINGto stir for a further 9 hours
3. 3
   استخلاصextracted with H2O
4. 4
   استخلاصThe organic phase was then extracted with brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   أخرىThe drying agent was removed by vacuum filtration
7. 7
   تركيزthe filtrate was concentrated

الإجراء التجريبي

5-(3,3-Dimethyl-but-1-ynyl)-3-[2-(ethoxy-methyl-phosphinoyl)-ethylamino]-thiophene-2-carboxylic acid methyl ester (233 mg, 0.629 mmol) was dissolved in pyridine (4 mL) and then 4-methyl-cyclohexanecarbonyl chloride (506 mg, 3.15 mmol) was added. The reaction was stirred for 7 hours at 100° C., the heat to the oil bath was shut off and the reaction was allowed to stir for a further 9 hours. The reaction was diluted with EtOAc and extracted with H2O. The organic phase was then extracted with brine and dried over Na2SO4. The drying agent was removed by vacuum filtration and the filtrate was concentrated. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (251 mg, 78%) was isolated from the residue by silica gel column chromatography.

المصدر