Реакция #43912

Уравнение реакции

3-(methylthio)-1-propanol

triethylamine

p-toluenesulfonyl chloride

N,N,N′,N′-tetramethyl-1,6-hexanediamine

→

title compound

Выход 94.0%

3-(methylthio)propyl 4-methylbenzenesulfonate

Выход 94.0%

Растворители

Water

toluene

toluene

Условия реакции

Обработка

1. 1
   Температураcooled
2. 2
   workup.ADDITIONAfter completion of the dropwise addition
3. 3
   Экстракцияthe mixture was extracted with ethyl acetate
4. 4
   ПромывкаThe extract was washed with saturated brine
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-40:60)

Методика

A solution of 3-(methylthio)-1-propanol (5.30 g, 50.0 mmol), triethylamine (10.5 mL, 75.0 mmol) and N,N,N′,N′-tetramethyl-1,6-hexanediamine (0.861 g, 5.00 mmol) in toluene (50 mL) was ice-cooled, and a solution of p-toluenesulfonyl chloride (14.3 g, 75.0 mmol) in toluene (50 mL) was added dropwise under nitrogen atmosphere. After completion of the dropwise addition, the mixture was stirred for 3 hr, during which the mixture was allowed to warm to room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-40:60) to give the title compound (12.2 g, yield 94%) as a colorless oil.

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