H2; sodium hydroxide in water

1: Et3N / H2O; dioxane / 96 h 2: 99 percent / BH3 / tetrahydrofuran / 1 h 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 4: CH2Cl2 / Ambient temperature 5: 90 percent / H2 / 10percent Pd/C / ethyl acetate 6: 97 percent / NaOH / methanol 7: 98 percent / BH3 / tetrahydrofuran / 1 h 8: 85 percent / Ph3P, CBr4 / tetrahydrofuran; acetonitrile / 24 h View Scheme

1: 95 percent / NaOH / dioxane 2: 91 percent / BH3*THF 3: 80 percent / pyridine*SO3, DMSO, Et3N View Scheme

1: Et3N / H2O; dioxane / 96 h 2: 99 percent / BH3 / tetrahydrofuran / 1 h 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 4: CH2Cl2 / Ambient temperature 5: 90 percent / H2 / 10percent Pd/C / ethyl acetate 6: 97 percent / NaOH / methanol 7: 98 percent / BH3 / tetrahydrofuran / 1 h View Scheme

1: Et3N / H2O; dioxane / 96 h 2: 99 percent / BH3 / tetrahydrofuran / 1 h 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, from -78 deg C to RT, 1.5 h 4: CH2Cl2 / Ambient temperature 5: 90 percent / H2 / 10percent Pd/C / ethyl acetate 6: 97 percent / NaOH / methanol View Scheme

sodium hydroxide in 1,4-dioxane

triethylamine in 1,4-dioxane; water 96 h;

acetyl chloride T=60°C; 7 h;