1: K2CO3 / methanol / 24 h / Ambient temperature 2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h 3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube 4: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C 5: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min 6: conc. HCl / methanol / 4.5 h / Heating 7: 61 percent / Jones reagent / acetone / 5 h / -30 °C View Scheme

1: K2CO3 / methanol 2: MnO2 / (COCl)2, DMSO and Et3N 3: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h 4: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating 5: PPTS / CH2Cl2 / 0.08 h / Ambient temperature 6: 1.) B2H6, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H2O2 / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min. 7: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C 8: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight 9: MeOH / PPTS / 0.08 h / Heating 10: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C 11: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C 12: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 13: PCC, sodium acetate / CH2Cl2 / 2.5 h 14: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 15: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 16: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

1: K2CO3 / methanol 2: MnO2 / (COCl)2, DMSO and Et3N 3: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h 4: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C / Heating 5: PPTS / CH2Cl2 / 0.08 h / Ambient temperature 6: 1.) B2H6, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H2O2 / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min. 7: 90 percent / triphenylphosphine, imidazole, I2 / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C 8: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight 9: MeOH / PPTS / 0.08 h / Heating 10: 1.) DMSO, (COCl)2 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min; 2.) CH2Cl2, -78 to 0 deg C 11: 35 percent / K2CO3, 18-crown-6 / toluene / 80 °C 12: H2O / PPTS / tetrahydrofuran / 1.5 h / Heating 13: PCC, sodium acetate / CH2Cl2 / 2.5 h 14: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min. 15: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C 16: 90 percent / KOH / aq. ethanol / 3 h / Heating View Scheme

With  potassium carbonate in  methanol T=0°C; 1 h;   

Multi-step reaction with 2 steps 1: K2CO3 / methanol / 24 h / Ambient temperature2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h  

Multi-step reaction with 3 steps 1: K2CO3 / methanol / 24 h / Ambient temperature2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube  

Multi-step reaction with 4 steps 1: K2CO3 / methanol / 24 h / Ambient temperature2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube4: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C  

Multi-step reaction with 5 steps 1: K2CO3 / methanol / 24 h / Ambient temperature2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li2CuCl4 / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube4: 85 percent / Br2, tert butylamine / toluene / 4 h / -78 - 5 °C5: 1.) CH3Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min