jones reagent in acetone; benzene T=0°C; 0.5 h;

1: 5-bromo-1-pentene With magnesium in diethyl ether 1 h; Inert atmosphere; 2: acrolein in diethyl ether T=-10°C; 1 h; Inert atmosphere; 3: With Jone's reagent in acetone T=0°C; Inert atmosphere;

1: 1) Mg / 1) ether, 1 h, 2) -10 deg C, 60 min 2: 89 percent / 2 M Jones reagent / acetone; benzene / 0.5 h / 0 °C View Scheme

1: (i) NaOEt, dioxane, (ii) (hydrolysis), (iii) aq. HCl 2: O2 / Pd / dimethylformamide; H2O 3: KOCMe2Et / toluene View Scheme

1: MeONa / methanol 2: NaBH4 / methanol 3: 1.) hydrolysis, 2.) heating View Scheme