反応 #56104

反応方程式

water

4-cyano-3,4-diphenylbutyryl chloride

2-butyn-1,4-diol

pyridine

→

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

溶媒

benzene

THF

反応条件

後処理

1. 1
   その他equipped with a Drierite tube
2. 2
   その他the layers were separated
3. 3
   抽出Two 60-ml ether extractions of the aqueous layer
4. 4
   洗浄were 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
   その他purified by column chromatography on silica gel (hexanes/methylene chloride)
7. 7
   その他to give two fractions

実験手順

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.

出典