Here's my crack at it: (adapted from something I saw regarding CPP...) I don't know ruby, but here's my best guess to what you were saying. (# to end of line. This also accounts for quotes that span multiple lines. )

#!/usr/bin/perl
$/ = undef;
$_ = <>;

s/([^#"']*(['][^']*['])|(["][^"]*["]))|([#][^\n]*)/defined $1 ? $1 : "
+"/gse;

print;
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Here's the input I tried.

# comment. 
"this is a quote" # end of line comment. 
print "this is a multiline quite. #right? 
";
No comments at all.
This is just general stuff. #this is a 'test too." '
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and the output was:

"this is a quote"
print "this is a multiline quote. # right?
";
No comments at all.
This is just general stuff.
[download]

Whaddya think? (I hope i typed the code in right. I do this on a separate machine)...