hydrogen; potassium carbonate; palladium 10 on activated carbon in water; isopropyl alcohol P=2250.23 Torr; 1 - 1.16667 h;

1: With acetic anhydride in toluene T=100°C; 16 h; 2: With hydrogenchloride in methanol; water 5 h; Heating / reflux; 3: With potassium carbonate in water pH=8; Purification / work up;

isopropylmagnesium chloride in tetrahydrofuran T=-20 - 20°C; 15 h;

hydrogen; potassium carbonate; palladium 10 on activated carbon in methanol; water Product distribution / selectivity;

hydrogen; potassium carbonate; palladium 10 on activated carbon in methanol; water 16 h; Product distribution / selectivity;

1: 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 16 h / 20 °C 2: palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide; water / 24 h / 80 °C / |Inert atmosphere 3: hydrogenchloride / methanol / 16 h / 20 °C 4: isopropylmagnesium chloride / tetrahydrofuran / 15 h / -20 - 20 °C View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran 1.2: -10 - 70 °C 2.1: 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 16 h / 20 °C 3.1: palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide; water / 24 h / 80 °C / |Inert atmosphere 4.1: hydrogenchloride / methanol / 16 h / 20 °C 5.1: isopropylmagnesium chloride / tetrahydrofuran / 15 h / -20 - 20 °C View Scheme

1: palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide; water / 24 h / 80 °C / |Inert atmosphere 2: hydrogenchloride / methanol / 16 h / 20 °C 3: isopropylmagnesium chloride / tetrahydrofuran / 15 h / -20 - 20 °C View Scheme

1: palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide; water / 24 h / 80 °C / |Inert atmosphere 2: hydrogenchloride / methanol / 16 h / 20 °C 3: isopropylmagnesium chloride / tetrahydrofuran / 15 h / -20 - 20 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 3.5 h / 20 °C 2: palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide; water / 24 h / 80 °C / |Inert atmosphere 3: hydrogenchloride / methanol / 16 h / 20 °C 4: isopropylmagnesium chloride / tetrahydrofuran / 15 h / -20 - 20 °C View Scheme