تفاعل #358118

معادلة التفاعل

3-cyclohexyl-2-(4-iodo-phenyl)-3-oxo-propionic acid methyl ester

sodium chloride

→

1-cyclohexyl-2-(4-iodo-phenyl)-ethanone

المردود 96.1%

المذيبات

water

water

dimethylsulfoxide

ظروف التفاعل

المعالجة

1. 1
   أخرىformed
2. 2
   درجة الحرارةThe reaction mixture was cooled to rt
3. 3
   استخلاصextracted thoroughly with ethyl acetate
4. 4
   غسيلThe combined organic extracts were washed with water (3 times), brine
5. 5
   تجفيفdried over sodium sulfate
6. 6
   تركيزconcentrated

الإجراء التجريبي

According to a modified literature procedure (Collins, I. et al J. Med. Chem. 2002, 45, 1887-1900) a solution of 5.06 g (13.1 mmol) of 3-cyclohexyl-2-(4-iodo-phenyl)-3-oxo-propionic acid methyl ester in 80 mL of dimethylsulfoxide (DMSO) was added a solution of 1.53 g (26.2 mmol) of sodium chloride (NaCl) in 5.8 mL of water (H2O), and the resulting mixture was heated at 150° C. for 3 h during which time a white solid formed. The reaction mixture was cooled to rt, poured into 500 mL of water, and extracted thoroughly with ethyl acetate. The combined organic extracts were washed with water (3 times), brine, dried over sodium sulfate and concentrated to give 4.13 g (96% yield) of desired 1-cyclohexyl-2-(4-iodo-phenyl)-ethanone as a yellow solid as indicated by 1H NMR (containing small traces of impurities). The product was used without any further purification in the next step.

المصدر