One more note as I didn't read the original carefully. I am not sure there is any way to upgrade the UA long haul booked on a code-share. If you had the SWU in your own account, you could do so. But you cannot get printed eSWUs to use on UA flights, only to use on LH flights. And I am not sure there is any way for the 1K to authorize your use of the eSWU since it cannot be requested in advance. You could try having the 1K request documenting the record in person, signing a "blue card" and carrying a signed authorization letter. But I do not know if this would happen, or work.

You can certainly ask your friend for a printed eSWU for the LH long haul. As to your odds of getting the upgrade, probably not wonderful as these are very popular upgrade routes. But day of the week, time of day, etc., can make a large difference. Also LH is making their own upgrades harder and more expensive so there will presumably be fewer LH passengers upgrading in the future.

Charles