[CH:1]1([CH:6]2[C:11]([O:12][CH3:13])=[CH:10][CH2:9][CH2:8][C:7]2=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].P([O-])([O-])(O)=O.[Na+].[Na+]>C1COCC1>[CH:1]1([C:6]2[C:7](=[O:14])[CH2:8][CH2:9][CH2:10][C:11]=2[O:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5]1To a solution of 2-cyclopentyl-3-methoxycyclohex-3-en-1-one (4.3 g) in dry THF (120 mL), sodium methoxide (1.1 g) was added in portions at room temperature. After stirring the reaction mixture at room temperature for 1.5 hours, cooled in an ice bath, and neutralized with sodium hydrogen phosphate solution. The organic layer was separated, aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting product was purified on a column of silica gel (Hex:EtOAc) to give the title compound as yellow liquid (2.82 g, 65.5%). 1H NMR (CDCl3): δ 1.25–1.8 (m, 8H, 4×CH2), 1.96 (m, 2H, CH2), 2.36 (t, 2H, CH2), 2.56 (t, 2H, CH2), 3.22 (m, 1H, CH), 3.79 (s, 3H, OCH3).
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