[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])([CH3:6])([CH3:5])[CH3:4].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])([CH3:6])([CH3:4])[CH3:5]To a tetrahydrofuran (THF) (10 ml) suspension of sodium hydride (60% in mineral oil) (68 mg, 1.7 mmol) was added a tetrahydrofuran (THF) solution (5 ml) of 4-tert-butyl-3-(2-methoxyethoxy)phenol (320 mg, 1.4 mmol) and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added ethyl bromoacetate (190 ul, 1.7 mmol) at ambient temperature. The stirred mixture was refluxed for 4 hours. The reaction mixture was then quenched with saturated aqueous solution of ammonium chloride and then crude products were extracted with ethyl acetate The organic layer was then washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=1/9 to furnish 0.26 g (60% yield) of the title compound as colorless oil.
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