1: With dimethylsulfide borane complex in tetrahydrofuran T=20°C; 12 h; 2: With sodium hydroxide; ethanol; dihydrogen peroxide in tetrahydrofuran T=20°C; 2 h; 3: With di-isopropyl azodicarboxylate; triphenylphosphine in tetrahydrofuran T=0 - 20°C; Mitsunobu reaction;

1.1: 91 percent / tetrahydrofuran; diethyl ether / 12 h / 20 °C 2.1: BH3*DMS / tetrahydrofuran / 12 h / 20 °C 2.2: aq. NaOH; aq. H2O2; EtOH / tetrahydrofuran / 2 h / 20 °C 2.3: 71 percent / DIAD; PPh3 / tetrahydrofuran / 0 - 20 °C View Scheme

potassium hydroxide; p-toluenesulfonyl chloride in tetrahydrofuran 0.5 h; Heating;

1: 100 percent / LAH / tetrahydrofuran / 1 h / 0 - 20 °C 2: TsCl; KOH / tetrahydrofuran / 0.5 h / Heating View Scheme