Originally Posted by UncleDave
... That plunger will be all the way back before the first drop of material makes it to the cylinder unless the line is impossibly short -...
No it won't, unless the line is impractically fat or long. Of course you'll get some air on the first pull, but not much on later ones if you evict the air before the oil.
Long ago, my father used an all-steel livestock syringe to empty the oil filter cartridge housing on the '54 Chevy. It worked well. On a typical modern plastic syringe not intended for oil, the syringe body, the piston, or the rubber piston rings might be chemically incompatible with oil.