Dichloromethane → (S)-6-methyl-5-decanone

Temperature

0 °C

After 0.78 ml (0.78 mmol) of diethylaluminum chloride (hexane 1M solution) were added to a dried methylene chloride (3 ml) solution of 81.8 mg (0.31 mmol) of (S)-3-butyl-2-methanesulfonyloxy-3-heptanol (urefined) 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)-6-methyl-5-decanone as a pale yellow oily substance (46.9 mg, yield 90%).

1. stirringstirred for two and a half hours at -78° C.
2. dry with materialdried with anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated
5. customThe oily residue was separated

ORD record

ord-37a4846632d448ddbd910b1cacfaee35

Source dataset

uspto-grants-1986_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04604486