[Mg].[Cu](C#N)C#N.F[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:18][CH:19]([C:23]2[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=2)C2OC2)C2OC2)=[CH:10][CH:9]=1.C(OCC)(=O)C.CCCCCC>C1COCC1>[CH2:14]([O:18][CH2:19][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:11]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1Magnesium (2.4 g, 98 mmol) was added to a 250 ml flask and flame dried. Dry THF, 25 ml, and 1 ml of dibromoethane were then added. 1-Bromo-4-6enzyloxy-butane 41 (12 g, 49.4 mmol) dissolved in 50 ml of dry THF was added dropwise and the reaction mixture was stirred at room temperature. After 1 hour, the reaction mixture is cooled in an ice-water bath and 90 mg of copper cyanide is added. After 10 minutes in an ice-bath, 4-fluorophenyl-glycidyl ether (5 g, 29.6 mmol) dissolved in 30 ml of dry THF is added slowly. The reaction is monitored by TLC (ethyl acetate:hexane 3:7). After 15 minutes, the reaction is quenched with saturated aqueous ammonium chloride, concentrated and partitioned between water-ethyl acetate. The ethyl acetate layer is then washed with brine, dried over Na2SO4 and concentrated to give the desired benzyloxy-heptane 42. The structure was confirmed by 1H-NMR.
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