triethylaluminum; toluene-4-sulfonic acid 1) CH2Cl2, 0 deg C, 20 h; 2) benzene; Yield given. Multistep reaction. Yields of byproduct given;

toluene-4-sulfonic acid 1) CH2Cl2, 0 deg C, 20 h; 2) benzene; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 1) NaNH2 / 1) ether, 45 min 2) ether, 24h, reflux 2: 1) NaH, EtOH, ethyl formate 2) mesyl azide / 1) ether a) 3.5h, -5 deg C b) 18h, 20 deg C 2) ether, 3.5d 3: 88 percent / K2CO3 / <Rh(OAc)2>2 / CH2Cl2 / 2 h / Ambient temperature 4: 1) Mg, Cu2I2 / 1) ether, THF, -25 deg C 2) a) -75 deg C, 30 min b) -5 deg C to 0 deg C, 4.5h 5: 9 percent / N2H4*H2O, K2CO3 / various solvent(s) / Heating View Scheme

1: 1) NaNH2 / 1) ether, 45 min 2) ether, 24h, reflux 2: 1) NaH, EtOH, ethyl formate 2) mesyl azide / 1) ether a) 3.5h, -5 deg C b) 18h, 20 deg C 2) ether, 3.5d 3: 88 percent / K2CO3 / <Rh(OAc)2>2 / CH2Cl2 / 2 h / Ambient temperature 4: 1) Mg, Cu2I2 / 1) ether, THF, -25 deg C 2) a) -75 deg C, 30 min b) -5 deg C to 0 deg C, 4.5h 5: 9 percent / N2H4*H2O, K2CO3 / various solvent(s) / Heating View Scheme

sodium borohydride in ethanol; water; acetone

sodium tetrahydroborate in methanol

Et2MeN*HI in water; toluene T=120°C; 6 h;

Yield given. Multistep reaction;