Reaktion #2146736

Reaktionsgleichung

quinoline

(9Z)-2,7-dimethyltridec-9-en-3-yne-2,5-diol

→

(3Z,9Z)-2,7-dimethyltrideca-3,9-diene-2,5-diol

Ausbeute 55.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was evacuated
2. 2
   Sonstigeflushed with nitrogen three times, and three times
3. 3
   Sonstigeevacuated
4. 4
   Sonstigeflushed with hydrogen
5. 5
   SonstigeThe resulting reaction mixture
6. 6
   Filtrationthe catalyst filtered off by suction over a pad of Celite
7. 7
   SonstigeAfter removal of the solvent
8. 8
   Sonstigein a rotary evaporator under reduced pressure
9. 9
   Sonstigethe resulting crude product (8.07 g) was purified by flash chromatography (100 g of silica gel, pentane/ether, 1:1, Rf=0.28)

Vorschrift

At room temp., 520 mg (0.488 mmol) of 10% palladium on barium sulphate and 190 mg (1.47 mmol) of quinoline were added to a stirred solution of 7.70 g (32.3 mmol) of this (9Z)-2,7-dimethyltridec-9-en-3-yne-2,5-diol in 170 mL of ethanol. The flask was evacuated and flushed with nitrogen three times, and three times evacuated and flushed with hydrogen. The resulting reaction mixture was then stirred for 1.5 h under an atmosphere of hydrogen at ambient pressure and temperature, prior to evacuation and ventilation with nitrogen. The reaction flask was opened to air, and the catalyst filtered off by suction over a pad of Celite. After removal of the solvent in a rotary evaporator under reduced pressure, the resulting crude product (8.07 g) was purified by flash chromatography (100 g of silica gel, pentane/ether, 1:1, Rf=0.28) to afford 4.28 g (55%) of (3Z,9Z)-2,7-dimethyltrideca-3,9-diene-2,5-diol as a colorless oil.

Quelle