1: KOH / aq. ethanol / 3 h / 70 °C 2: CH2Cl2 / 2 h / 23 °C 3: 96 percent / H2 / Pd(OH)2 / ethyl acetate / 12 h 4: 1.) 1-(chlorocarbonyl)-1-methylene acetate, 2.) NaOMe / 1.) CHCl3, 23 deg C, 3 h, 2.) THF, 23 deg C, 4 h 5: 75 percent / propan-2-ol / 2 h / Heating View Scheme

1: KOH / ethanol; H2O / 17 h / Heating 2: CH2Cl2 / 3 h / 23 °C 3: 356 mg / H2 / Pd(OH)2 / ethyl acetate; methanol / 12 h View Scheme

1: KOH / ethanol; H2O / 17 h / Heating 2: CH2Cl2 / 3 h / 23 °C 3: 356 mg / H2 / Pd(OH)2 / ethyl acetate; methanol / 12 h 4: 61 percent / PPh3, DEAD / CHCl3 / 72 h / Heating View Scheme

1: KOH / ethanol; H2O / 17 h / Heating 2: CH2Cl2 / 3 h / 23 °C 3: 356 mg / H2 / Pd(OH)2 / ethyl acetate; methanol / 12 h 4: 61 percent / PPh3, DEAD / CHCl3 / 72 h / Heating View Scheme

1: KOH / ethanol; H2O / 17 h / Heating 2: CH2Cl2 / 3 h / 23 °C 3: 356 mg / H2 / Pd(OH)2 / ethyl acetate; methanol / 12 h 4: 61 percent / PPh3, DEAD / CHCl3 / 72 h / Heating 5: propan-2-ol / 3.5 h / 68 °C View Scheme