4-(N,N-dimethlyamino)pyridine; TEA in tetrahydrofuran; N,N-dimethyl-formamide Heating;

1: 1.) CuI / 1.) Et2O 2: 80 percent / TEA, DMAP / tetrahydrofuran; dimethylformamide / Heating View Scheme

1: 1.) O3, 2.) Me2S / 1.) MeOH, - 60 deg C 2: 1.) NaH / 1.) THF 3: 54 percent / dibal / diethyl ether / -78 - 0 °C 4: 1.) Pyr-SO3, 2.) LiAlH4 / 1.) THF 5: 97 percent / 48percent aq. HF / acetonitrile / 0 °C View Scheme

1: 1.) O3, 2.) Me2S / 1.) MeOH, - 60 deg C 2: 1.) NaH / 1.) THF 3: 54 percent / dibal / diethyl ether / -78 - 0 °C 4: 1.) Pyr-SO3, 2.) LiAlH4 / 1.) THF View Scheme

1: 1.) O3, 2.) Me2S / 1.) MeOH, - 60 deg C 2: 1.) NaH / 1.) THF 3: 14 percent / dibal / diethyl ether / -78 - 0 °C View Scheme