HT1535 Songs won't transfer from iTunes to iPod touch

I'm having trouble transferring music from iTunes onto my iPod touch (5th gen). When I plug my iPod into my computer and try to drag songs onto it from my iTunes library, it says 'updating files' but gets then gets stuck. I keep trying and have waited for over 30 minutes for one song to transfer but it just isn't working. The songs show up in my iPod's music library but they are greyed out and do not show up on my actual iPod. Also, when I tried to transfer purchased from my ipod to iTunes, I kept getting an error message but that has now worked. There is plenty of free space on my ipod so that can't be the problem. This is a recent problem and I was able to do both of these tasks easily a couple of weeks ago. My iPod is up to date and I updated iTunes in case that was the problem but it has not helped. I've ran out of ideas and don't know what else to do now! Has anyone had this problem and managed to solve it?

Find one of the songs in iTunes that won't sync to the iPod, and try to play it (just double click the file in iTunes). Do you get an error message? If so, let us know what it is, as this will probably explain why it can't be transferred to the iPod.
CG

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