Hydrochloric Acid → HCID 66692279, compound

Participants

Reaction Conditions

Reaction Steps

1.5 M LDA in cyclohexane (1.34 ml; 2 mmol; Aldrich) was added to 4-hydroxy-6-methyl-3-(3-phenylpropanoyl)-2-pyrone (258.27 mg; 1 mmol; Example 1.1) in 8.4 ml anhydrous THF, and the reaction mixture was stirred under N2 for 0.5 h at 0° C. 1-iodo-butane (136.8 μl; 1.2 mmol; Aldrich) and HMPA (167 ul; 0.96 mmol: Aldrich) were added sequentially under N2, and the reaction mixture was stirred under N2 for 2 h at 0° C. and 5 h at room temperature. The reaction mixture was acidified by addition of 1 N HCl (16 ml) and extracted with ethyl acetate (3×20 ml). The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. The product was isolated by chromatography on silica gel. Yield: 20%. MS (MALDI): calculated, m/z 315.2 (MH+); found, 315.1.

Provenance & Evidence