Reacción #343467

ord-7c12282e7d874b62b9f30688a8362156

Ecuación de reacción

OC1CCSCC1
tetrahydro-4H-thiopyran-4-ol
Cc1ccc(S(=O)(=O)Cl)cc1
4-methylphenylsulfonyl chloride
O
water
Cc1ccc(S(=O)(=O)OC2CCSCC2)cc1
product
Rendimiento 142.0%
Cc1ccc(S(=O)(=O)OC2CCSCC2)cc1
Tetrahydro-4H-thiopyran-4-yl 4-methylphenylsulfonate
Rendimiento 142.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe whole extracted with diethyl ether
  2. 2
    LavadoThe organic phase was washed with water
  3. 3
    Secadowith a 10% aqueous solution of sodium hydroxide, dried
  4. 4
    Concentraciónconcentrated

Procedimiento

To a solution of 4.1 g (0.015 mole) of tetrahydro-4H-thiopyran-4-ol in 40 mL of pyridine, cooled in an ice bath, was added 2.90 g (0.15 mole) of 4-methylphenylsulfonyl chloride, and the reaction mixture was stirred at room temperature for 16 hours. The mixture was poured into a mixture of ice and water, and the whole extracted with diethyl ether. The organic phase was washed with water then with a 10% aqueous solution of sodium hydroxide, dried, and concentrated to give 5.8 g of product as an oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04702763uspto-grants-1987_10