12,12-Difluoro-11-dodecen-2-ol → Methyl 10,10-difluoro-9-decenyl ketone

Participants

Reaction Steps

To a stirred solution of 1.0 gram (0.0045 mole) of 12,12-difluoro-11-dodecen-2-ol (prepared in Example 3) in 10 ml of acetone was added 1.68 ml (0.0045 mole) of Jones reagent (2.7 Molar in acetone) while maintaining the reaction mixture temperature at 20°-25° C. Excess Jones reagent was destroyed by the addition of 1-methylethanol. The reaction mixture was passed through silica gel with the aid of additional acetone. The eluate was concentrated under reduced pressure, and the residue was dissolved in 50 ml of pentane. The resultant solution was washed with two 20 ml portions of water and then with one 20 ml portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 0.65 gram of methyl 10,10-difluoro-9-decenyl ketone. The nmr spectrum was consistent with the proposed structure. The reaction was repeated several times.

Provenance & Evidence