Reacción #43912

Ecuación de reacción

3-(methylthio)-1-propanol

triethylamine

p-toluenesulfonyl chloride

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

→

title compound

Rendimiento 94.0%

3-(methylthio)propyl 4-methylbenzenesulfonate

Rendimiento 94.0%

Disolventes

Water

toluene

toluene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente