C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.N1([C:23](=[O:31])[CH2:24][CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][O:27]2)C=CN=C1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[O:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][CH2:24][C:23]([CH:13]1[C:14](=[O:17])[CH2:15][CH2:16][O:11][CH2:12]1)=[O:31]Lithium bis(trimethylsilyl)amide (1.283 ml, 6.83 mmol) was added to a stirred solution of tetrahydro-4H-pyran-4-one (0.601 ml, 6.51 mmol) in toluene (3 mL) at 0° C. and the resulting mixture was stirred for 2 minutes. 1-(1H-imidazol-1-yl)-3-(tetrahydrofuran-2-yl)propan-1-one (0.632 g, 3.25 mmol) toluene (1 mL) was added and the reaction mixture was stirred for 5 minutes before it was quenched with acetic acid (0.559 ml, 9.76 mmol) in water (4 mL). The organic layer was separated and purified by flash column chromatography (ethyl acetate in heptane, 0 to 40%) yielding 3-(3-(tetrahydrofuran-2-yl)propanoyl)dihydro-2H-pyran-4(3H)-one (117 mg, 16%).
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