4-(N,N-dimethlyamino)pyridine; sodium hydride; triethylamine; p-toluenesulfonyl chloride 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 1) TsCl, Et3N, DMAP, 2) NaH / 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h 2: BF3*OEt2 / CH2Cl2 / 0 - 20 °C View Scheme

1: 1) TsCl, Et3N, DMAP, 2) NaH / 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h 2: 99 percent / BF3*OEt2 / CH2Cl2 / 0 - 20 °C View Scheme

1: 1) TsCl, Et3N, DMAP, 2) NaH / 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h 2: 1) CuI / 1) Et2O, -10 deg C, 20 min, 2) Et2O, THF, -78 deg C to 0 deg C, 2 h View Scheme

1: 1) TsCl, Et3N, DMAP, 2) NaH / 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h 2: 77 percent / tetrahydrofuran / 1.5 h / -78 °C View Scheme