sodium hydroxide in 2-methoxy-ethanol 4 h; Ambient temperature;

1: 1.) n-BuLi / 1.) THF, hexane, -100 deg C to -95 deg C, 10 min, 2.) THF, hexane, -100 deg C to -95 deg C, 10 min 2: 94 percent / aq. NaOH / 2-methoxy-ethanol / 15 h / Heating 3: HCl conc. / 4 h / Heating 4: 39 percent / H2, HCl conc. / Pd / dioxane / 20 h / 40 - 48 °C 5: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h 6: 82 percent / diphenyl ether / 4 h / 190 - 205 °C 7: 56 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature 8: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature 9: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 10: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 11: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) DMF, 0 -5 deg C, 20 min, 2.) DMF, RT, 20 h 2: NaCN / dimethylsulfoxide / 2 h / 180 - 185 °C 3: 5percent HCl 4: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h 5: 82 percent / diphenyl ether / 4 h / 190 - 205 °C 6: 56 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature 7: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature 8: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 9: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 10: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: 5percent HCl 2: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h 3: 82 percent / diphenyl ether / 4 h / 190 - 205 °C 4: 56 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature 5: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature 6: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 7: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 8: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 2: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: 82 percent / diphenyl ether / 4 h / 190 - 205 °C 2: 56 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature 3: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature 4: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 5: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 6: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 2: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: NaCN / dimethylsulfoxide / 2 h / 180 - 185 °C 2: 5percent HCl 3: 1.) NaH, 2.) KH / 1.) THF, reflux, 2.) THF, reflux, 2 h 4: 82 percent / diphenyl ether / 4 h / 190 - 205 °C 5: 56 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature 6: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature 7: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 8: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 9: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 2: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 3: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme

1: 61 percent / DDQ / acetic acid / 18 h / Ambient temperature 2: 80 percent / 10percent NaOH / 2-methoxy-ethanol / 18 h / Ambient temperature 3: 1.) Et3N, isobutyl chloroformate / 1.) DMSO, 1.5 h, 2.) DMSO, RT, 22 h 4: 73 percent / NaOH / 2-methoxy-ethanol / 4 h / Ambient temperature View Scheme