in ethyl acetate

hydrogen; palladium on activated charcoal in ethyl acetate

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 1.2: 73 percent / tetrahydrofuran / 9 h / 0 °C 2.1: 95 percent / DDQ / toluene / Heating 3.1: (CH3)3SnSn(CH3)3 / Pd(PPh3)4 / tetrahydrofuran / Heating 3.2: 120 mg / CuBr / Pd(PPh3)4 / tetrahydrofuran / Heating 4.1: 100 percent / H2 / 10 percent Pd/C / ethyl acetate / 40 - 45 <unit not given> View Scheme

1.1: (CH3)3SnSn(CH3)3 / Pd(PPh3)4 / tetrahydrofuran / Heating 1.2: 120 mg / CuBr / Pd(PPh3)4 / tetrahydrofuran / Heating 2.1: 100 percent / H2 / 10 percent Pd/C / ethyl acetate / 40 - 45 <unit not given> View Scheme