Itunes doesn't sync music that was transferred from an external hard drive

I transferred a song from an external hard drive onto itunes on my laptop. The song plays through itunes on my laptop after I've disconnected the external hard drive, but it won't sync the song to my iPhone. I have a lot of music on that ext. HD and I'd like to listen to it on my iPhone.

Hi, Alex 58.
Thank you for visiting Apple Support Communities.
Try opening iTunes with the external drive connected and sync the music over to the iPhone. If all media is located on the external drive, iTunes will not sync the requested media to the device without the drive connected. You may need to remove the sync music preference and reapply it for the media to transfer.
iTunes 11 for Windows: Set up syncing for iPod, iPhone, or iPad
http://support.apple.com/kb/ph12313
Cheers,
Jason H.

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I tried moving all my media to an external hard drive to make room on my MacBook Pro and just be able to run the media (ie music movies etc) from the external hard drive when it was connected.
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PS I am running Mac OS X Lion version 10.7.5 and iTunes 11.1.3 (8) 64-bit

2012EVOL wrote:
Hello,
I tried moving all my media to an external hard drive to make room on my MacBook Pro and just be able to run the media (ie music movies etc) from the external hard drive when it was connected.
Quit iTunes.
Copy the entire /Music/iTunes/ folder to the external. Don't only copy the iTunes media folder.
Hold Option, launch iTunes, select Choose library... and select the iTunes folder on the external.
This is all you need to do.
Everything for iTunes (except the application) is on the external.
2nd I think (this was back in March 2013) I decided to cut/delete the folder Automatically Add to iTunes and moved it to one of my external hard drives (this folder for some reason contained mostly everythiing that was in the iTunes Media folder).
Make a shortcut to this folder on your desktop.
Nothing should be in this folder. When you put a file here, it will get moved by iTunes and added to the library.
The reason it had files in it is because you moved it.

Itunes doesn't sync music that was transferred from an external hard drive

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