تفاعل #56104

معادلة التفاعل

water

4-cyano-3,4-diphenylbutyryl chloride

2-butyn-1,4-diol

pyridine

→

4-Hydroxy-2-butynyl 4-Cyano-3,4-diphenylbutyrate

المذيبات

benzene

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with a Drierite tube
2. 2
   أخرىthe layers were separated
3. 3
   استخلاصTwo 60-ml ether extractions of the aqueous layer
4. 4
   غسيلwere washed twice with 100 ml of H2O, with 100 ml saturated aqueous sodium bicarbonate
5. 5
   workup.STIRRINGwith 100 ml saturated aqueous sodium chloride and were stirred over MgSO4
6. 6
   أخرىpurified by column chromatography on silica gel (hexanes/methylene chloride)
7. 7
   أخرىto give two fractions

الإجراء التجريبي

A solution of 10.7 g (0.038 mol) of 4-cyano-3,4-diphenylbutyryl chloride in 30 ml of benzene was added over a 45 minute period to a stirred solution of 6.5 g (0.076 mol) of 2-butyn-1,4-diol and 3.4 ml of pyridine in 100 ml of THF at 0°. The reaction mixture was stirred for 24 hours at room temperature in a flask equipped with a Drierite tube. The solution was poured into 50 ml of water and the layers were separated. Two 60-ml ether extractions of the aqueous layer were combined with the THF layer, were washed twice with 100 ml of H2O, with 100 ml saturated aqueous sodium bicarbonate, and with 100 ml saturated aqueous sodium chloride and were stirred over MgSO4. The filtered solution was stripped and purified by column chromatography on silica gel (hexanes/methylene chloride) to give two fractions weighing 12.6 g (47%) having different isomer ratios as determined from the nmr spectra. The infrared and nmr spectra are in accord with the assigned structure.

المصدر