تفاعل #5767

معادلة التفاعل

water

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

diisobutyl aluminium hydride

hexane ethyl acetate

→

sarcophytol A

المردود 90.3%

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىOne hour
2. 2
   تجفيفby drying over MgSO4, filtration, and concentration
3. 3
   أخرىto give a residue, which

الإجراء التجريبي

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%).

المصدر