Is it possible to make the mold 3 parts instead of 2? Maybe have a rod up the middle that once removed allows that section to bend or fold to get it out?
You can cover the narrow opening with a thin film (like sheet wax) and do a two part mold. After casting, the thin resin covering the opening can be easily removed and cleaned up. I think you should be able to pull the center plug of rubber out of the larger end if your silicone isn't too stiff.
I think combining these two methods to make a 2-part mold will work well--
Stage 1: Apply a film across the smaller of the two openings, and mold the outside/bottom half of the part (considering the end with the small opening as the "bottom"). There are a few ways this can be done, such as: A) suspend the part securely above the bottom of the mold box and simply pour the bottom half of the mold around the outside of it, or B) put the part into a box which is made so one end can be removed without destroying the box, with the large opening of the part against the removable end, then embed the part halfway in clay so that the half with the covered small opening is exposed. Pour the mold half, then when cured remove the end of the box and clean out the clay before molding the other half.
Stage 2: After the bottom half of the mold has cured, suspend a cylindrical plug somewhat smaller in diameter than the larger opening, inside the part as shown below, being sure it doesn't touch the part, then apply mold release and mold the top half of the part including the outside and inside. If the plug is a material that might get stuck to the mold, apply mold release to its bottom end before suspending it in the part.
When the mold has cured, you first remove the plug and it will no longer be needed. Then the top part of the 2-part mold will be easy to remove, since there is now space for the interior portion to be squished into so it can easily fit through the opening in the part. As Irken Tech wrote, your castings from this 2-part mold will probably have a resin skin across the small opening where the film was separating the mold parts, but this will easily be trimmed away.
