تفاعل #76407

معادلة التفاعل

water

Methanesulfonyl chloride

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

triethylamine

→

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

المردود 64.3%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىthe temperature of the mixture below 5° C
2. 2
   استخلاصThe suspension is extracted with ethyl acetate
3. 3
   استخلاصthe organic extract
4. 4
   غسيلis washed neutral with water
5. 5
   تجفيفwith brine, and dried over magnesium sulfate
6. 6
   أخرىRotary evaporation of the solvent and recrystallization from 50 ml of ethanol

الإجراء التجريبي

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).

المصدر