[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([CH3:19])([CH2:14][C:15]#[C:16][CH2:17][CH3:18])[C:9](OCC)=[O:10].[OH-].[Na+]>CCOCC>[CH3:7][C:8]([CH3:19])([CH2:14][C:15]#[C:16][CH2:17][CH3:18])[CH2:9][OH:10]To a slurry of LiAlH4 (7.4 g, 194 mmol) in anhydrous Et2O (200 ml) at 0° C. was added a solution of ethyl 2,2-dimethylhept-4-ynoate (29 g, 159 mmol) in anhydrous Et2O (100 ml) slowly over a period of 30 min. The reaction mixture was stirred at 0° C. for 3 hours. A 10% aqueous solution of NaOH (35 ml) was added slowly. The solid was filtered off. The filtrate was washed with brine, dried (MgSO4) and the solvent was removed under reduced pressure to afford the titled compound as a colorless liquid (20 g, 89%). TLC: Pet. ether/EtOAc (8/2): Rf=0.3. 1H NMR (CDCl3, 300 MHz) δ 0.95 (6H, s), 1.03 (3H, t), 1.81 (1H, br. s), 2.10 (2H, s), 2.17 (2H, m), 3.14 (2H, s).
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