1: LiAlH4 / tetrahydrofuran / 1.5 h / Heating 2: 12.1 g / Na / liquid ammonia; diethyl ether / 1.5 h / -78 °C View Scheme

sodium ethanolate in ethanol T=20 - 50°C; 36 h;

trifluoroacetic acid in dichloromethane T=20°C; 24 h;

1.1: n-BuLi / hexane; tetrahydrofuran / 0.67 h / -78 °C 1.2: 93 percent / tetrahydrofuran; hexane 2.1: 75 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 2 h / Heating 3.1: ethanol / 14 h / Heating 3.2: 71 percent / aq. NaOH / ethanol / 3 h / Heating 4.1: 71 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 5.1: 53 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1.1: 75 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 2 h / Heating 2.1: ethanol / 14 h / Heating 2.2: 71 percent / aq. NaOH / ethanol / 3 h / Heating 3.1: 71 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 4.1: 53 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1: 71 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 2: 53 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1.1: ethanol / 14 h / Heating 1.2: 71 percent / aq. NaOH / ethanol / 3 h / Heating 2.1: 71 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 3.1: 53 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C View Scheme