[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[H-].[Na+].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>CN(C=O)C>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8])=[CH:16][CH:15]=1A 250 mL round-bottom flask equipped with stir bar was charged with 7-octen-1-ol (1.20 mL, 7.80 mmol). Anhydrous DMF (60 mL) was added, and the solution was allowed to cool to 0° C. (ice-bath). Sodium hydride (2.40 g, 40.0 mmol) was added in portions, and the mixture was allowed to stir until gas evolution ceased. p-Methoxybenzyl chloride (2.1 mL, 16 mmol) was added by a syringe and the mixture was allowed to stir for 24 h. The reaction was quenched by addition of a saturated aqueous solution of sodium bicarbonate (100 mL), and washed with ethyl acetate (5×100 mL). The combined organic layers were washed with water (3×100 mL) to remove dmf, further washed in brine (1×50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting yellow oil was purified by silica gel chromatography (96:4 hexanes:EtOAc), delivering 1-methoxy-4-((oct-7-en1-yloxy)methyl)benzene (946 mg, 3.81 mmol, 49.0% yield) as a colorless oil. IR (neat): 3074 (w), 2998 (m), 2929 (m), 2854 (w), 1640 (m), 1613 (w), 1586 (w), 1511 (m), 1463 (m), 1441 (w), 1361 (w), 1301 (m), 1245 (s), 1208 (w), 1172 (m), 1095 (s), 1036 (s), 995 (w), 909 (m), 819 (s), 755 (w), 727 (w), 707 (w), 637 (w), 571 (w), 513 (w), 418 (w); 1H NMR (400 MHz, CDCl3): δ 7.25 (2H, d, J=8.8 Hz), 6.87 (2H, d, J=8.4 Hz), 5.80 (1H, m), 4.98 (1H, dd, J=17.2, 2.0 Hz), 4.92 (1H, dd, J=10.0, 2.4 Hz), 4.42 (2H, s), 3.79 (3H, s), 3.43 (2H, t, J=6.6 Hz), 2.03 (2H, app q, J=6.9 Hz), 1.63-1.56 (2H, m), 1.41-1.27 (6H, m); 13C NMR (100 MHz, CDCl3): δ 159.2, 139.2, 130.9, 129.3, 114.3, 113.8, 72.6, 70.3, 55.3, 33.8, 29.8, 29.1, 29.0, 26.2; HRMS (ESI+) [M+NH4]+ calcd for C16H28NO2: 266.2120, found: 266.2130.
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