C[O:2][C:3](=O)[CH2:4][C:5]([CH3:13])([C:7]1[O:8][C:9]([CH3:12])=[CH:10][CH:11]=1)[CH3:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:13][C:5]([C:7]1[O:8][C:9]([CH3:12])=[CH:10][CH:11]=1)([CH3:6])[CH2:4][CH2:3][OH:2]Step D To a solution of 3-methyl-3-(5-methyl-furan-2-yl)-butyric acid methyl ester (1.5 g, 7.8 mmol) in anhydrous tetrahydrofuran (50 mL) at 0° C. was added a tetrahydrofuran solution (1 M) of LiAlH4 (10 mL, 10 mmol) under nitrogen. The reaction mixture was stirred at 0° C. for 1 h, then poured into a ice-water. The mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 3-methyl-3-(5-methyl-furan-2-yl)-butan-1-ol as a yellow oil (1.2 g, 77%).
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