sodium hydroxide; sulfuric acid; acetic acid in water; ethyl acetate

1: 94 percent / toluene / 1 h / Heating 2: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / 4 h 3: 99 percent / LiBH4 / diethyl ether / 15 h / Ambient temperature 4: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 5: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 6: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 7: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 8: CF3COOH, H2O View Scheme

1: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / 4 h 2: 99 percent / LiBH4 / diethyl ether / 15 h / Ambient temperature 3: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 4: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 5: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 6: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 7: CF3COOH, H2O View Scheme

1.1: 68 percent / aq. NaOH / ethanol / 48 h / 38 °C 2.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 3.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 4.1: aq. NaOH / 2 h / 20 °C 4.2: aq. H2SO4 / 3 h / 0 °C 4.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 View Scheme

1.1: 90 percent / CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C 2.1: 91 percent / H2O; ethyl acetate / 24 h / 50 °C 3.1: aq. NaOH / 2 h / 20 °C 3.2: aq. H2SO4 / 3 h / 0 °C 3.3: 57 percent / aq. NaOH / 1 h / 20 °C / pH 7 View Scheme

sodium hydroxide in methanol T=40 - 50°C; 24 h; Inert atmosphere;

1: 98 percent / Pd(OAc)2 2: 72 percent / NaOH / ethanol 3: 90 percent / CH3SO2Cl; Et3N 4: 91 percent / ethyl acetate; H2O / 24 h / 50 °C 5: 57 percent View Scheme

1: 87 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -60 °C 2: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 3: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 4: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 5: CF3COOH, H2O View Scheme

1: 1) t-BuOK / 1) THF, toluene, 10 min, 2) toluene, 0 deg C, 20 min 2: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 3: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 4: CF3COOH, H2O View Scheme

1: 1) CH2Cl2, molecular sieves 3A, UV, 0 - 5 deg C 2: 74 percent / 1 M BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / Heating 3: CF3COOH, H2O View Scheme