My guess is too thin and too long of extension cord causing voltage drop when the air conditioner comes on, then there may be an EMS system that shuts it down on low voltage to save the air conditioner from burning out.
A better solution would be a 30 amp rated extension cord with the 30 amp to 15 amp dogbone located near the outlet. Don't use one of those 30 to 15 puck adapters running an air conditioner as they tend to overheat.
p.s. that 30 to 50 amp dogbone in the middle only draws power from one side of the 50 amp plug. So no power is coming through that second extension cord.