1: 1. NaH 2. NaBH4, glacial HOAc / 1. ether, a) reflux b) cooling (ice-water) c) reflux, 10 min 2: 91 percent / tetrahydrofuran / 3 h / 0 °C 3: 1. Na2CO3 2. HCl / 1. dioxane, 0 deg C (ice-water bath) View Scheme

1: 91 percent / tetrahydrofuran / 3 h / 0 °C 2: 1. Na2CO3 2. HCl / 1. dioxane, 0 deg C (ice-water bath) View Scheme

1: 1. chlorine / 1. 60 deg C, 1 h 2. DMF, reflux, 2 h 2: 1. NaH 2. NaBH4, glacial HOAc / 1. ether, a) reflux b) cooling (ice-water) c) reflux, 10 min 3: 91 percent / tetrahydrofuran / 3 h / 0 °C 4: 1. Na2CO3 2. HCl / 1. dioxane, 0 deg C (ice-water bath) View Scheme

hydrogenchloride; sodium carbonate 1. dioxane, 0 deg C (ice-water bath); Yield given. Multistep reaction;