1.1: sodium hydroxide / water 2.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 2.2: 1 h / -65 - -60 °C 3.1: thionyl chloride / 10 °C / Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 5.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: sodium hydroxide / water 2.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 2.2: 1 h / -65 - -60 °C 3.1: thionyl chloride / 10 °C / Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 5.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C 6.1: dichloromethane / 1.5 h / 0 - 5 °C 6.2: 1 h / 0 - 5 °C View Scheme

1.1: sodium hydroxide / water 2.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 2.2: 1 h / -65 - -60 °C 3.1: thionyl chloride / 10 °C / Reflux View Scheme

1.1: sodium hydroxide / water 2.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 2.2: 1 h / -65 - -60 °C View Scheme

sodium hydroxide in water