sodium hydride in ethylene glycol dimethyl ether 10 h;

1: Mg / methanol / 6 h / Ambient temperature 2: 85 percent / N,N-di-isopropylethylamine / CH2Cl2 / 24 h / Ambient temperature 3: LiN(SiMe3)2 / tetrahydrofuran / 0 °C 4: KOH / aq. ethanol / 48 h / Heating 5: LiAlH4 / tetrahydrofuran / 1) 0 deg C, 2) r.t. 6: CH2Cl2; pyridine / 1) 0 deg C, 2) r.t. 7: 40 percent / LiEt3BH / tetrahydrofuran / 1) r.t., 2) reflux, 4 h 8: oxalyl chloride, Et3N / dimethylsulfoxide / -78 °C 10: ZnBr2 / CH2Cl2 View Scheme