Реакция #76407

Уравнение реакции

water

Methanesulfonyl chloride

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

triethylamine

→

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

Выход 64.3%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеthe temperature of the mixture below 5° C
2. 2
   ЭкстракцияThe suspension is extracted with ethyl acetate
3. 3
   Экстракцияthe organic extract
4. 4
   Промывкаis washed neutral with water
5. 5
   Сушкаwith brine, and dried over magnesium sulfate
6. 6
   ДругоеRotary evaporation of the solvent and recrystallization from 50 ml of ethanol

Методика

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).

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