1: With lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 0.5 h; 2: With sulfuric acid in tetrahydrofuran; methanol

1: With 9-bora-bicyclo[3.3.1]nonane in tetrahydrofuran T=50°C; 1 h; Inert atmosphere; 2: With sodium perborate; water in tetrahydrofuran T=20°C; Inert atmosphere;

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / 0 - 20 °C / |Inert atmosphere 1.2: 20 °C / |Inert atmosphere 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 50 °C / |Inert atmosphere 2.2: 20 °C / |Inert atmosphere View Scheme

aluminium trichloride in tetrachloromethane

n-butyllithium 1.) diethyl ether, 2.) diethyl ether, 0 deg C; Yield given. Multistep reaction;