re = /^(\w+)\s+([\w-]+)$\n/m
str = '5067235721 24-FEB-16
5067245417 24-FEB-16
5067212004 10-FEB-16
5067148322 22-FEB-16
5067148330 19-FEB-16
5067148349 17-FEB-16
5067148357 17-FEB-16
5067148365 18-FEB-16
5067148373 17-FEB-16
5067148284 23-FEB-16
5067148292 23-FEB-16
5067148306 23-FEB-16
'
subst = ' select \\1, to_date(\'\\2\') from dual;\\nunion\\n'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html