1: 1.) potassium 2-methyl-2-butanolate / 1.) hexamethylphosphoric triamide, 0 deg C, 15 min, 2.) benzene, 20 deg C, 1 h 2: 87 percent / H2 / 10percent Pd/C / ethyl acetate View Scheme

1: 89 percent / toluene / 48 h / Heating 2: 1.) potassium 2-methyl-2-butanolate / 1.) hexamethylphosphoric triamide, 0 deg C, 15 min, 2.) benzene, 20 deg C, 1 h 3: 87 percent / H2 / 10percent Pd/C / ethyl acetate View Scheme

1: 79 percent / K2CO3 / acetone / 48 h / Heating 2: 97.5 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 81 percent / MnO2 / acetone / 1 h / 23 °C 4: 1.) potassium 2-methyl-2-butanolate / 1.) hexamethylphosphoric triamide, 0 deg C, 15 min, 2.) benzene, 20 deg C, 1 h 5: 87 percent / H2 / 10percent Pd/C / ethyl acetate View Scheme

1: 97.5 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 81 percent / MnO2 / acetone / 1 h / 23 °C 3: 1.) potassium 2-methyl-2-butanolate / 1.) hexamethylphosphoric triamide, 0 deg C, 15 min, 2.) benzene, 20 deg C, 1 h 4: 87 percent / H2 / 10percent Pd/C / ethyl acetate View Scheme

1: 81 percent / MnO2 / acetone / 1 h / 23 °C 2: 1.) potassium 2-methyl-2-butanolate / 1.) hexamethylphosphoric triamide, 0 deg C, 15 min, 2.) benzene, 20 deg C, 1 h 3: 87 percent / H2 / 10percent Pd/C / ethyl acetate View Scheme

1: 1.) potassium 2-methyl-2-butanolate / 1.) hexamethylphosphoric triamide, 0 deg C, 15 min, 2.) benzene, 20 deg C, 1 h 2: 87 percent / H2 / 10percent Pd/C / ethyl acetate View Scheme

in pyridine 24 h; Heating;

1: 95 percent / H2 / 5percent Pd-C / acetic acid; ethyl acetate 2: 94 percent / pyridine / 24 h / Heating View Scheme

1: 1.) toluene-p-sulphonic acid / 1.) dichloromethane, 19 deg C, 6 h, 2.) CH2Cl2, 40 deg C, 2 h 2: 10percent KOH / H2O / Heating View Scheme