반응 #5767

반응 방정식

water

2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one

diisobutyl aluminium hydride

hexane ethyl acetate

→

sarcophytol A

수율 90.3%

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타One hour
2. 2
   건조by drying over MgSO4, filtration, and concentration
3. 3
   기타to give a residue, which

실험 절차

To the above ketone compound, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one (137 mg, 0.48 mmol) in dry toluene (2.5 ml) was dropwise added with stirring on a cooling bath at -70° C. a solution of 1M diisobutyl aluminium hydride in toluene (0.6 ml). One hour later, disappearance of the starting material was confirmed. After addition of water (0.25 ml) and removal of the cooling bath, the reaction mixture was stirred, followed by drying over MgSO4, filtration, and concentration to give a residue, which was subjected to silica gel column chromatography (solvent:-hexane/ethyl acetate=12:1) to obtain the aimed sarcophytol A (125 mg, 88%).

출처