반응 #2146736

반응 방정식

quinoline

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

→

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

수율 55.1%

용매

ethanol

반응 조건

후처리

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

실험 절차

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.

출처