Reaktion #51136

Reaktionsgleichung

Mesylate

methyl 4-{3-[(methylsulfonyl)oxy]propyl}bicyclo-[2.2.2]octane-1-carboxylate

sodium ethanethiolate

→

methyl 4-[3-(ethylthio)propyl]bicyclo[2.2.2]octane-1-carboxylate

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed twice with 1N aqueous HCl
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Sonstigeevaporated

Vorschrift

Mesylate 11-5 (3.30 g, 10.9 mmol) was dissolved in DMF (20 mL) and treated with sodium ethanethiolate (1.82 g, 21.7 mmol). The solution was stirred at 45° C. for 3 h, then the mixture was diluted with 100 mL of ethyl acetate and washed twice with 1N aqueous HCl, then with saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated to afford methyl 4-[3-(ethylthio)propyl]bicyclo[2.2.2]octane-1-carboxylate (11-6) as a crude oil which was used without purification in the next step.

Quelle