methyl 11-oxoundecanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 7.5 grams (0.035 mole) of methyl 11-oxoundecanoate and 14.7 grams (0.07 mole) of dibromodifluoromethane was cooled to 0°-10° C., and a solution of 18.4 grams (0.07 mole) of triphenylphosphine in 50 ml of dimethylacetamide was added dropwise. During the addition the temperature of the reaction mixture was maintained at 0°-10° C. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature, and 4.6 grams (0.07 mole) of zinc dust was added in two portions. The addition caused an exothermic reaction which raised the temperature of the reaction mixture to 90° C. The reaction mixture was allowed to cool to ambient temperature where it stood without stirring for 60 hours. The reaction mixture was diluted with water and was subjected to a steam distillation with pentane. The appropriate fractions were combined and concentrated under reduced pressure yielding 4.3 grams of methyl 12,12-difluoro-11-dodecenoate. The nmr spectrum was consistent with the proposed structure. was cooled to 0°-10° C. During the addition the temperature of the reaction mixture was maintained at 0°-10° C Upon completion of addition the reaction mixture The addition an exothermic reaction which raised the temperature of the reaction mixture to 90° C to cool to ambient temperature where it was subjected to a steam distillation with pentane concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 11-undecanoate-[1,3]dioxolane (the cyclic acetal of methyl 11-oxoundecanoate): MS (ESI-positive, CH3OH, m/z): 281.2 (MNa+, calc. 281.4).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dimethylsulfoxide, 178 ml, was heated to 150° C. as nitrogen was bubbled through it. Sodium bicarbonate, 23.7 grams (0.282 mole), was added portionwise while maintaining the reaction mixture temperature at 140°-160° C. Upon completion of addition, 13.6 grams (0.037 mole) of methyl 11-(4-methylphenylsulfonyloxy)undecanoate was added portionwise during a ten minute period. Upon completion of addition the reaction mixture was allowed to cool to ambient temperature, and then it was poured into 600 ml of ice-water. The mixture was stirred until the ice melted, and then it was extracted with three portions of heptane. The combined extracts were washed with three portions of water followed by two portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 7.8 grams of methyl 11-oxoundecanoate. The nmr spectrum was consistent with the proposed structure. was bubbled through it Sodium bicarbonate, 23.7 grams (0.282 mole), was added portionwise while maintaining the reaction mixture temperature at 140°-160° C was added portionwise during a ten minute period Upon completion of addition the reaction mixture it was extracted with three portions of heptane The combined extracts were washed with three portions of water The organic layer was dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure