[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.CO[C:10](=[O:13])[O:11][CH3:12].COC1C=[C:18]2[C:22](=[CH:23]C=1)[C:21](=[O:25])[CH2:20][CH2:19]2>C(OCC)(=O)C>[CH3:12][O:11][C:10]([CH:20]1[CH2:19][C:18]2[C:22](=[CH:23][C:7]([O:6][CH3:5])=[CH:3][CH:4]=2)[C:21]1=[O:25])=[O:13]Combine NaH (5.4 g, 122.1 mmol), THF anhydrous (150 mL), and dimethylcarbonate (6.6 mL, 81.3 mmol). While refluxing the reaction under a nitrogen atmosphere, add dropwise 5-Methoxyindanone (3.46 g, 21.33 mmol) over one hour. After the reaction mixture refluxes for 12 hours, quench using Acetic acid and then add Ethyl acetate to the reaction mixture in a separatory funnel. Wash the organic layer several times with water and dry the organic layer over Na2SO4 followed by concentration under reduced pressure. Flash Chromatograph using 1:1 Hexanes:Ethyl acetate to afford 3.14 g, 14.3 mmol (67% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 3.3-3.4 (1H, dd), 3.5-3.6 (1H, dd), 3.7-3.8 (1H, m), 3.8 (3H, s), 3.9 (3H, s), 6.8-7.0 (2H, m), 7.7-7.8 (1H, m); TLC 2:1 Hexanes:Ethyl acetate Rf:=0.4.
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