Did Satan know that Jesus would rise from the grave?
It is impossible to answer this question with certainty since, as far as I’m aware, there is no passage in Scripture that answers this question definitively (cf. Deut. 29:29). However, we can glean from several scriptural passages that it was at least a possibility that Satan knew ahead of time that Jesus would rise again.
For one, Christ and the apostles stated that his resurrection was “in accordance with the Scriptures” (Lk. 24:46; John 20:9; Acts 2:25-32; 13:33-35; 26:22-23; 1 Cor. 15:4; cf. Ps. 16:8-11; Is. 53:10). Satan was familiar with the Scripture (Matt. 4:6), so it is possible that he was aware of these Old Testament prophecies about Christ’s resurrection. Jesus’ rebuke of Peter, calling him Satan when Peter tried to dissuade him from going to Jerusalem so he could die and be resurrected (Matt. 16:21-23), might indicate that Satan was trying to use Peter to tempt Jesus from going through with his plan to save mankind by dying and coming back to life.
However, it is also possible that, even being aware of the Old Testament prophecies of Jesus’ death and resurrection, he might have misinterpreted them as did many of the Jews (cf. 1 Cor. 2:6-8). It is possible that by successfully tempting Judas and the scribes and Pharisees to betray and kill Jesus, Satan might have mistakenly thought he had won and thus would have been very much dismayed and surprised on the following Sunday morning when Jesus was resurrected.
In the end, as far as I’m aware, there’s nothing in Scripture that could point to a definite answer to this question.