تفاعل #1005979

معادلة التفاعل

ethyl 4-(2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)-thio-chromen-6-ylethynyl)-benzoate

tert-butyllithium

4-ethylbromobenzene

→

Ethyl 4-[[4-(4-ethylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate

المذيبات

pentane

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىto give a yellow solution
2. 2
   درجة الحرارةThis solution was heated to 50° C. for 1 hour
3. 3
   درجة الحرارةcooled to room temperature
4. 4
   أخرىthe reaction quenched by the addition of saturated aqueous NH4Cl
5. 5
   استخلاصThe solution was extracted with EtOAc
6. 6
   غسيلthe combined organic layers were washed with H2O and saturated aqueous NaCl
7. 7
   تجفيفbefore being dried (MgSO4)
8. 8
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

A solution of 4-ethylbromobenzene (670.9 mg, 3.63 mmol) in 4.0 mL of THF was cooled to −78° C.; and tert-butyllithium (464.5 mg, 7.25 mmol, 4.26 mL of a 1.7M solution in pentane) was added to give a yellow solution. After 30 minutes a solution of ZnCl2 (658.7 mg, 4.83 mmol) in 8.0 mL THF was slowly added via cannula. The resulting solution was warmed to room temperature and transferred via cannula to a solution of ethyl 4-(2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)-thio-chromen-6-ylethynyl)-benzoate (1.20 g, 2.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (111.7 mg, 0.097 mmol) in 8.0 mL THF. This solution was heated to 50° C. for 1 hour, cooled to room temperature, and the reaction quenched by the addition of saturated aqueous NH4Cl. The solution was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. Ethyl 4-[[4-(4-ethylphenyl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate was isolated by column chromatography (5% EtOAc/hexanes) as a colorless oil.

المصدر