Reacción #216466

Ecuación de reacción

water

Sodium hydride

benzyl mercaptan

3-n-Propyloxetan-3-ylmethyl methanesulphonate

→

2,2-Di-(benzylthiomethyl)pentan-1-ol

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at 0° C. for 1 hour
2. 2
   TemperaturaThe mixture was refluxed
3. 3
   workup.STIRRINGwith stirring for 6 hours
4. 4
   TemperaturaThe mixture was cooled
5. 5
   ExtracciónThe aqueous mixture was extracted with diethyl ether
6. 6
   LavadoThe ethereal extracts were washed with water
7. 7
   Secadodried over anhydrous magnesium sulphate
8. 8
   Otroevaporated in vacuo
9. 9
   OtroThe residue was chromatographed on silica
10. 10
    Lavadoeluting with 1:4

Procedimiento

A solution of benzyl mercaptan (25.0 ml) in dry dimethylformamide (100 ml) was stirred at 0° C., under a current of nitrogen. Sodium hydride (6.0 g., 80% dispersion in oil) was added carefully and the mixture was stirred at 0° for 1 hour. 3-n-Propyloxetan-3-ylmethyl methanesulphonate (10.0 g.) was added and the mixture was stirred at 0° C. for 1 hour. The mixture was refluxed with stirring for 6 hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was chromatographed on silica, eluting with 1:4; diethyl ether: hexane. 2,2-Di-(benzylthiomethyl)pentan-1-ol was obtained as a pale yellow oil (15.6 g.)

Fuente