Hydrogen Peroxide → 11-Dodecen-1-ol, 12,12-difluoro-

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Reaction Conditions

Reaction Steps

Three grams (0.o15 mole) of 1,1-difluoro-1,11-dodecadiene (prepared in Example 3, Step B) was stirred while being cooled to 0° C. After this time 5 ml (0.005 mole) of borane-tetrahydrofuran complex (1 Molar in tetrahydrofuran) was added dropwise. Upon completion of addition, the reaction mixture was stirred for 30 minutes, and then, in turn, 5 ml of aqueous 3 Normal sodium hydroxide and 5 ml of aqueous 30% hydrogen peroxide were added dropwise. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure to a residue. The residue was stirred with 25 ml of water, and the mixture was extracted with three 15 ml portions of methylene chloride. The combined extracts were washed with two 15 ml portions 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 to a residual oil. The oil was evacuated under reduced pressure at 135° C., and then it was subjected to column chromatography on silica gel. Elution was accomplished using heptane and methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure yielding 0.74 gram of 12,12-difluoro-11-dodecen-1-ol. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence