[CH:1]([CH:4]1[C:9]([O:10][CH3:11])=[CH:8][CH2:7][CH2:6][C:5]1=[O:12])([CH3:3])[CH3:2].C[O-].[Na+].P([O-])([O-])(O)=O.[Na+].[Na+]>C1COCC1>[CH:1]([C:4]1[C:5](=[O:12])[CH2:6][CH2:7][CH2:8][C:9]=1[O:10][CH3:11])([CH3:3])[CH3:2]To a solution of 2-isopropyl-3-methoxy-cyclohex-3-enone (6 g) in dry THF (120 mL), sodium methoxide (1.5 g) was added in portions at room temperature. After stirring at room temperature for 1.5 hours, the reaction mixture was cooled in an ice bath and neutralized with 10% sodium hydrogen phosphate solution. The organic layer was separated, then the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, then 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 a yellow liquid (5.4 g, 90%). 1H NMR (CDCl3): δ 1.09 (d, 6H, 2×CH3), 1.95 (m, 2H, CH2), 2.31 (t, 2H, CH2), 2.54 (t, 2H, CH2), 3.2 (m, 1H, CH), 3.78 (s, 3H, OCH3).
Loading…
