I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1OC.[CH2:10]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22]C#N)[CH2:16][CH2:15]1)[CH2:11][CH2:12][CH3:13].S(=O)(=O)(O)O.[OH-].[Na+].CC[O:34][CH2:35][CH3:36]>C(Cl)Cl.CO.C1COCC1>[CH2:10]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:35]([C:36]2[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:3])=[O:34])[CH2:16][CH2:15]1)[CH2:11][CH2:12][CH3:13]In a 25 mL oven-dried flask was charged Mg turnings (125 mg, 5.2 mmol) which were activated by the use of a heat-gun. Under inert atmosphere was added a suspension of 2-iodoanisole (1.13 g, 5.2 rmmol) in Et2O (4 mL) and the reaction mixture was allowed to stand at rt for 1 hour. Compound 4 (720 mg, 3.4 mmol) dissolved in Et2O (4 mL) was added and the mixture was refluxed over-night. THF (15 mL) and sulfuric acid (4 mL, 2 M) was added and the reaction mixture was stirred for 4 h, followed by addition of NaOH (6 mL, 2 M). The reaction mixture was extracted with ethyl acetate (3×50 mL), and the combined organic phases were evaporated to dryness to produce 1.2 g of crude 5. The crude product was subjected to CC [eluent: CH2Cl2:CH3OH (99:1)] to give pure 5 (0.42 g, 26%). 1H NMR (CDCl3) δ 0.83 (t, 3H), 1.20-1.42 (m, 9H), 1.65-1.73 (d, 2H), 1.96-2.20 (m, 4H), 2.53 (t, 2H), 3.02-3.17 (m, 4H), 3.89 (s, 3H), 6.95-7.01 (m, 2H), 7.44 (t, 1H), 7.65 (d, 1H).
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