sodium hydroxide; ethyl (Z)-2-n-propyl-2,4-pentadienoate T=25°C; 24 h;

1: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 20 min; 2) THF, hexane, -78 deg C, 15 min 2: Et3N / CH2Cl2 / 1 h / 0 °C 3: KH / tetrahydrofuran / 12 h / Ambient temperature 4: aq. NaOH, ethyl (Z)-2-n-propyl-2,4-pentadienoate / 24 h / 25 °C View Scheme

1: Et3N / CH2Cl2 / 1 h / 0 °C 2: KH / tetrahydrofuran / 12 h / Ambient temperature 3: aq. NaOH, ethyl (Z)-2-n-propyl-2,4-pentadienoate / 24 h / 25 °C View Scheme

1: triphenylcarbenium tetrafluoroborate, collidine / CH2Cl2 / 0.5 h / Ambient temperature 2: aq. NaOH, ethyl (Z)-2-n-propyl-2,4-pentadienoate / 24 h / 25 °C View Scheme