Reaktion #2467548

Reaktionsgleichung

1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho p-toluenesulfonate

triethylamine

thiotetronic acid

cyclododecylbutanoic acid

→

white solid

Ausbeute 33.4%

3-(4-cyclododecyl-1-oxobutyl)-4-hydroxyl-2-(5H)thiophenone

Ausbeute 33.4%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for 10 minutes
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGis stirred overnight
4. 4
   SonstigeThe reaction mixture is quenched with 1N HCl
5. 5
   SonstigeThe layers are separated
6. 6
   Waschenthe aqueous phase is washed once with dichloromethane
7. 7
   WaschenThe combined organic layers are washed twice with aqueous sodium bicarbonate and twice with aqueous 2N HCl
8. 8
   TrocknenThe organic phase is then dried over MgSO4
9. 9
   Sonstigethe dichloromethane evaporated
10. 10
    Sonstigechromatographed on acidic silica gel using 8% ether/hexanes
11. 11
    workup.DISSOLUTIONdissolved in ether
12. 12
    Waschenwashed with 1N HCl
13. 13
    Sonstigedried
14. 14
    Sonstigeevaporated

Vorschrift

To a dry flask under N2 atmosphere at 0° C. is added 1.31 g (11.3 mmol) of thiotetronic acid in 40 mL of dry dichloromethane followed by 1.42 mL (10.2 mmol) of triethylamine and 0.38 g (3.1 mmol) of 4-dimethylaminopyridine. After stirring at 0° C. for 5 minutes, 2.6 g (10.2 mmol) of cyclododecylbutanoic acid is added followed by 4.8 g (11.3 mmol) of 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho p-toluenesulfonate. After stirring for 10 minutes, the reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction mixture is quenched with 1N HCl. The layers are separated and the aqueous phase is washed once with dichloromethane. The combined organic layers are washed twice with aqueous sodium bicarbonate and twice with aqueous 2N HCl. The organic phase is then dried over MgSO4 and the dichloromethane evaporated. The residue is flash chromatographed on acidic silica gel using 8% ether/hexanes, dissolved in ether, washed with 1N HCl, dried and evaporated to give 1.2 g of a white solid: m.p. 62°-69° C.; IR; NMR (CDCl3) δ1.2-1.4 (m, 10H), 1.5 (s, 4H), 1.65 (m, 2H), 2.9 (t, 2H, J=7 Hz), 3.9 (s, 2H); MS Anal. Calc'd. for C20H32O3S: C, 68.53; H, 8.63 Found: C, 67.72; H, 8.84

Quelle