Reacción #343469

Ecuación de reacción

water

4-methylphenylsulfonyl chloride

tetrahydrothiophene-3-ol

4-methylphenylsulfonyl chloride

→

product

Rendimiento 50.6%

3-Tetrahydrothienyl 4-methylphenylsulfonate

Rendimiento 50.6%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   workup.STIRRINGwas stirred for 1 hour
3. 3
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 64 hours
4. 4
   Extracciónthe whole was extracted with methylene chloride
5. 5
   SecadoThe methylene chloride solution was dried
6. 6
   Concentraciónconcentrated

Procedimiento

To a chilled solution of 1.12 g (0.0098 mole) of tetrahydrothiophene-3-ol in 15 mL of pyridine was added 1.91 g (0.01 mole) of 4-methylphenylsulfonyl chloride, and the reaction mixture was stirred in the cold, about 16° C., for 1 hour then placed in a cold refrigerator for 16 hours. The reaction mixture was allowed to warm to room temperature and was stirred for 1 hour. An additional 0.3 g (0.0016 mole) of 4-methylphenylsulfonyl chloride was added, and the reaction mixture was stirred at room temperature for 64 hours. The reaction mixture was poured into water, and the whole was extracted with methylene chloride. The methylene chloride solution was dried and concentrated to give 1.28 g of product as an oil.

Fuente