Reaktion #451516

Reaktionsgleichung

diethylaluminum chloride

methylene chloride

(S)-2-methanesulfonyloxy-3-octyl-3-undecanol

→

(S)-10-methyl-9-octadecanone

Ausbeute 90.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for two and a half hours at -78° C.
2. 2
   Trocknendried with anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe oily residue was separated

Vorschrift

After 0.63 ml (0.63 mmol) of diethylaluminum chloride (hexane 1M solution) were added to a dried methylene chloride (3 ml) solution of 89.7 mg (0.24 mmol) of (S)-2-methanesulfonyloxy-3-octyl-3-undecanol (unrefined) at -78° C. under stirring, and stirred for two and a half hours at -78° C., the temperature was raised to 0° C. over an hour and a half. The reaction was stopped with three drops of phosphoric acid buffer solution (pH 7). The resultant suspension was diluted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated. The oily residue was separated and refined by the use of silica gel column chromatography (hexane/ethyl acetate=35/1) to obtain (S)-10-methyl-9-octadecanone as a colorless oily substance (60.5 mg, yield 90%).

Quelle