반응 #76407

반응 방정식

water

Methanesulfonyl chloride

2-Hydroxyimino-4-p-tolyl-but-3-enenitrile

triethylamine

→

2-methanesulfonyloxyimino-4-p-tolyl-but-3-enenitrile

수율 64.3%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타the temperature of the mixture below 5° C
2. 2
   추출The suspension is extracted with ethyl acetate
3. 3
   추출the organic extract
4. 4
   세척is washed neutral with water
5. 5
   건조with brine, and dried over magnesium sulfate
6. 6
   기타Rotary evaporation of the solvent and recrystallization from 50 ml of ethanol

실험 절차

2-Hydroxyimino-4-p-tolyl-but-3-enenitrile (1.9 g; 0.01 mol) is dissolved in 15 ml of anhydrous tetrahydrofuran, and cooled to 0° C. Methanesulfonyl chloride (0.93 ml, 0.012 mol) is added at once, followed by triethylamine (2.1 ml, 0.015 mol) dropwise over 20 min, keeping the temperature of the mixture below 5° C. The mixture is then stirred at 5-10° C. for 3.5 hours, and poured into 200 ml of iced water. The suspension is extracted with ethyl acetate, the organic extract is washed neutral with water, then with brine, and dried over magnesium sulfate. Rotary evaporation of the solvent and recrystallization from 50 ml of ethanol yields 2-methanesulfonyloxyimino-4-p-tolyl-but-3-enenitrile (1.7 g; 64%) as off-white crystals, mp 134-135° C. with one part melting at 145° C. 1H-NMR reveals the presence of two isomers (probably E/Z around the imino double bond).

출처