Frozen, thawed, and refrozen?
Trying to extract that with light hydrocarbons without first removing the water seems problematic at best.
Running cold “locks up” the water, but the water “locks up” the goods you’re after.
Seems to me your viable options are run above zero, (cleaning up the crude and your solvent will be a pain.) or remove the water.
Can you set up a decent cold trap?
…that X10 might work
Use your vac oven…Converting vac oven to freeze dryer
Your stuff is currently frozen, sucking on it causes evaporative cooling. I’ve lyophilized hundreds of plant and fungal samples without bothering to freeze them first. DNA & psychoactives both preserved beautifully…
Notice that the sample containers are not “cooled”.
Pre-freezing is absolutely recommended, but from there you just suck until the evaporative cooling stops and they warm up because they are done…