hydrogen; platinum(IV) oxide in ethanol

1: 1.) O3, NaHCO3, 2.) Et3N / 1.) CH2Cl2, MeOH, 2.) CH2Cl2, a) 0 deg C, 15 min, b) RT, 4 h 2: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 3: H2 / Pd/C / acetone 4: 5percent aq. NaOH / methanol 5: 1.) Et3N / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, 30 min 6: CH2Cl2 / 1 h View Scheme

1: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 2: H2 / Pd/C / acetone 3: 5percent aq. NaOH / methanol 4: 1.) Et3N / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, 30 min 5: CH2Cl2 / 1 h View Scheme

1: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 2: H2 / Pd/C / acetone 3: 5percent aq. NaOH / methanol 4: 1.) Et3N / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, 30 min 5: CH2Cl2 / 1 h View Scheme

hydrogen; platinum(IV) oxide in ethanol 1.25 h; Ambient temperature;

1: 2.) lithium aluminium hydride, 3.) aq. H2SO4 / 1.) ethanol 2: 9.22 g / H2 / 5percent palladium-charcoal / ethyl acetate / 1.5 h / Ambient temperature 3: 1.) sodium ethoxide, 2.) 10percent methanolic potassium hydroxide / 1.) room temperature, 19 h, 2.) 22 h 4: 1.) oxalyl chloride / 1.) ether, 18 h 5: 42 mg / H2 / pre-reduced platinum oxide / ethanol / 1.25 h / Ambient temperature View Scheme

1: 9.22 g / H2 / 5percent palladium-charcoal / ethyl acetate / 1.5 h / Ambient temperature 2: 1.) sodium ethoxide, 2.) 10percent methanolic potassium hydroxide / 1.) room temperature, 19 h, 2.) 22 h 3: 1.) oxalyl chloride / 1.) ether, 18 h 4: 42 mg / H2 / pre-reduced platinum oxide / ethanol / 1.25 h / Ambient temperature View Scheme

1: 1.) sodium ethoxide, 2.) 10percent methanolic potassium hydroxide / 1.) room temperature, 19 h, 2.) 22 h 2: 1.) oxalyl chloride / 1.) ether, 18 h 3: 42 mg / H2 / pre-reduced platinum oxide / ethanol / 1.25 h / Ambient temperature View Scheme

1: 1.) oxalyl chloride / 1.) ether, 18 h 2: 42 mg / H2 / pre-reduced platinum oxide / ethanol / 1.25 h / Ambient temperature View Scheme

1: 1.) Et3N / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, 30 min 2: CH2Cl2 / 1 h View Scheme