[CH2:1](Br)[C:2]#[CH:3].C([O-])([O-])=O.[K+].[K+].[CH3:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15]>CC(C)=O>[CH2:3]([CH:13]([C:12](=[O:17])[CH3:11])[C:14](=[O:16])[CH3:15])[C:2]#[CH:1]The mixture of propargyl bromide (0.32 g, 2.70 mmol), K2CO3 (2.22 g, 16.10 mmol), and 2,4-pentane-dione (1.34 g, 13.40 mmol) in acetone (30 mL) was stirred for 24 hrs at 60° C. After filtration and removal of solvent under reduced pressure, the crude residue was purified by flash chromatography (hexane) to give 22 as colorless liquid (0.30 g, 69%). 1HNMR (400 MHz, CDCl3) δ 2.03-2.04 (t, J=5.28 Hz, 1H), 2.22 (s, 3H), 2.25 (s, 3H), 2.68-2.71 (m, 2H), 3.84-3.87 (t, J=15.08 Hz, 1H); 13CNMR (100 MHz, CDCl3) δ 14.45, 29.33, 29.41, 68.70, 70.79, 86.13, 202.18, 202.63.
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