1: NaH / diethyl ether; ethanol / 2 h / Heating 2: pyridine 3: 28 percent / LDA / tetrahydrofuran / 1.) 30 min, -78 deg C, 2.) 30 min, 0 deg C 4: Br2 / tetrahydrofuran; CHCl3 / 0.75 h / -78 °C 5: NaBH4 / ethanol; tetrahydrofuran; CHCl3 / -78 °C 6: HgCl2, CaCO3 / acetonitrile; H2O / 48 h / Ambient temperature 7: pyridine View Scheme

1: Br2 / tetrahydrofuran; CHCl3 / 0.75 h / -78 °C 2: NaBH4 / ethanol; tetrahydrofuran; CHCl3 / -78 °C 3: HgCl2, CaCO3 / acetonitrile; H2O / 48 h / Ambient temperature 4: pyridine View Scheme

1: 28 percent / LDA / tetrahydrofuran / 1.) 30 min, -78 deg C, 2.) 30 min, 0 deg C 2: Br2 / tetrahydrofuran; CHCl3 / 0.75 h / -78 °C 3: NaBH4 / ethanol; tetrahydrofuran; CHCl3 / -78 °C 4: HgCl2, CaCO3 / acetonitrile; H2O / 48 h / Ambient temperature 5: pyridine View Scheme

1: pyridine 2: 28 percent / LDA / tetrahydrofuran / 1.) 30 min, -78 deg C, 2.) 30 min, 0 deg C 3: Br2 / tetrahydrofuran; CHCl3 / 0.75 h / -78 °C 4: NaBH4 / ethanol; tetrahydrofuran; CHCl3 / -78 °C 5: HgCl2, CaCO3 / acetonitrile; H2O / 48 h / Ambient temperature 6: pyridine View Scheme

Yield given. Multistep reaction;

pyridine