[CH3:1][O:2][C:3]1([O:9][CH3:10])[CH2:6][CH:5]([CH2:7][OH:8])[CH2:4]1.CC(C)([O-])C.[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[CH3:1][O:2][C:3]1([O:9][CH3:10])[CH2:6][CH:5]([CH2:7][O:8][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4]1To a stirring solution of crude (3,3-dimethoxy-cyclobutyl)-methanol (11.9 g, 81.5 mmol) in 100 mL of tetrahydrofuran at room temperature was added a solution of potassium t-butoxide (163 mL, 1M tetrahydrofuran). The reaction was allowed to stir for 30 minutes and then benzyl bromide (10.2 mL, 85.6 mmol) was added. After 30 minutes TLC analysis indicated complete consumption of starting material. The reaction was quenched with water and diluted with methylene chloride. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification of this material was accomplished by flash column chromatography using a Biotage Column 75 medium, eluting with a gradient of hexanes through 5% EtOAc/hexanes. The product containing fractions were collected and concentrated under reduced pressure to give the title compound (13.2 g, 69% yield), as a colorless oil.
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