Which will undergo deprotonation most readily in basic medium?

Due to the presence of two electron-withdrawing carbonyl group the methylene protons are very much acidic. The $-\mathrm{M}$ effect of $-{\mathrm{COCH}}_3$ is more than $-\mathrm{COOMe}$. Hence, the acidic nature of acetyl acetone is more than rest of the two molecules.