1: LiAlH4 / diethyl ether 2: aq. HCl, NaNO2 View Scheme

1.1: 47 percent / dicyclohexylcarbodiimide; copper(I) chloride / diethyl ether / 12 h 2.1: potassium tert-butoxide; 18-crown-6 / tetrahydrofuran / 1 h / 0 °C 2.2: 87 percent / tetrahydrofuran / 0.25 h / -78 °C 3.1: 51 percent / sodium nitrite; acetic acid / dimethylsulfoxide / 28 h / 40 °C 4.1: 62 percent / lithium; NH3 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / -78 °C View Scheme

H-Y zeolite in toluene 8 h; Heating;

dicyclohexyl-carbodiimide; copper(l) chloride in diethyl ether Dehydration; 12 h; Title compound not separated from byproducts;

indium; acetic acid in tetrahydrofuran 50 h; Heating;

oxidation;