C[O:2][C:3](=O)[CH2:4][C:5]([CH2:9][CH3:10])([CH3:8])[CH2:6][CH3:7].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:6]([C:5]([CH3:8])([CH2:9][CH3:10])[CH2:4][CH2:3][OH:2])[CH3:7]Step C To a solution of 3-ethyl-3-methyl-pentanoic acid methyl ester (1.5 g, 9.4 mmol) in anhydrous tetrahydrofuran (30 mL) at 0° C. was added a tetrahydrofuran solution (2 M) of LiAlH4 (5 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-ethyl-3-methyl-pentan-1-ol as a yellow oil (1.3 g, 100%).
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