Reaktion #216466

Reaktionsgleichung

water

Sodium hydride

benzyl mercaptan

3-n-Propyloxetan-3-ylmethyl methanesulphonate

→

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

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 0° C. for 1 hour
2. 2
   TemperaturThe mixture was refluxed
3. 3
   workup.STIRRINGwith stirring for 6 hours
4. 4
   TemperaturThe mixture was cooled
5. 5
   ExtraktionThe aqueous mixture was extracted with diethyl ether
6. 6
   WaschenThe ethereal extracts were washed with water
7. 7
   Trocknendried over anhydrous magnesium sulphate
8. 8
   Sonstigeevaporated in vacuo
9. 9
   SonstigeThe residue was chromatographed on silica
10. 10
    Wascheneluting with 1:4

Vorschrift

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.)

Quelle