1: 31 percent / DDQ / dioxane / 10 h / Heating 2: H2 / tris(triphenylphosphine)-rhodium chloride / benzene 3: 47 percent / NaBH4 / pyridine / 20 h / Ambient temperature View Scheme

1: 9 g / N,N-dimethylaminopyridine, Et3N / CH2Cl2 / 0.5 h 2: 138 mg / Br2 / acetic acid / 1 h / Ambient temperature 3: 62 mg / Cr(OAc)2 / CHCl3; acetic acid / 1 h / Ambient temperature 4: 26 mg / Li2CO3, LiBr / dimethylformamide / 4 h / 80 °C 5: 30 percent H2O2, 2 N NaOH / dioxane / 24 h / Ambient temperature 6: diethyl ether 7: 58 mg / Cr(OAc)2 / ethanol / 1 h / Ambient temperature 8: 15 mg / NaBH4 / propan-2-ol / 0.5 h 9: 178 mg / 2 N LiOH / methanol / 1 h / Heating View Scheme