sodium hydride in tetrahydrofuran T=20°C; Alkylation; 14 h;

1.1: n-butyl lithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 77 percent / tri-isopropyl borate / tetrahydrofuran / 4 h / -78 - -20 °C 2.1: 88 percent / trifluoroacetic acid / CH2Cl2 3.1: 61 percent / potassium carbonate / acetonitrile View Scheme

1.1: n-butyl lithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 77 percent / tri-isopropyl borate / tetrahydrofuran / 4 h / -78 - -20 °C 2.1: 88 percent / trifluoroacetic acid / CH2Cl2 View Scheme