hydrogen; palladium on activated charcoal in ethanol

1: 3.1 percent / glacial HOAc, HCl(g) / H2O / Heating 2: 1) NaH / 1) DMF, 0 deg C, 25 min, 2) DMF, RT, 2 h 3: H2 / 5percent Pd/c / ethanol View Scheme

1: 3.1 percent / glacial HOAc, HCl(g) / H2O / Heating 2: 1) NaH / 1) DMF, 0 deg C, 25 min, 2) DMF, RT, 2 h 3: H2 / 5percent Pd/c / ethanol View Scheme

1: 54 percent / t-BuOK / dimethylsulfoxide; 2-methyl-propan-2-ol / Ambient temperature 2: 43 percent / various solvent(s) / 4.5 h / 186 - 190 °C 3: 1) NaH / 1) DMF, 0 deg C, 25 min, 2) DMF, RT, 2 h 4: H2 / 5percent Pd/c / ethanol View Scheme

1: 43 percent / various solvent(s) / 4.5 h / 186 - 190 °C 2: 1) NaH / 1) DMF, 0 deg C, 25 min, 2) DMF, RT, 2 h 3: H2 / 5percent Pd/c / ethanol View Scheme

1: 1) NaH / 1) DMF, 0 deg C, 25 min, 2) DMF, RT, 2 h 2: H2 / 5percent Pd/c / ethanol View Scheme