triethylamine in dichloromethane T=0°C; 1 h;

1: t-BuONO / tetrahydrofuran / Heating 2: LiAlH4 / tetrahydrofuran / Heating View Scheme

hydrogen; palladium on activated charcoal in ethanol Ambient temperature;

potassium hydroxide 1.5 h; Heating;

1: 86 percent / H2 / 5percent Pd/C / methanol / 3 h / Ambient temperature 2: 90 percent / CH2Cl2 / 48 h / Ambient temperature 3: 1.) sodium hydride, DMSO, triphenylmethane / 1.) RT, 2.) 10 min 4: 86 percent / 10percent KOH / 1.5 h / Heating View Scheme

1: 89 percent / tetrahydrofuran; diethyl ether / 1.) -20 deg C, 0.5 h, 2.) 0 deg C, 1 h 2: 86 percent / H2 / 5percent Pd/C / methanol / 3 h / Ambient temperature 3: 90 percent / CH2Cl2 / 48 h / Ambient temperature 4: 1.) sodium hydride, DMSO, triphenylmethane / 1.) RT, 2.) 10 min 5: 86 percent / 10percent KOH / 1.5 h / Heating View Scheme

1: 99 percent / thionyl chloride / CH2Cl2 / 1.) -10 deg C, 2 h, 2.) RT, overnight 2: 89 percent / tetrahydrofuran; diethyl ether / 1.) -20 deg C, 0.5 h, 2.) 0 deg C, 1 h 3: 86 percent / H2 / 5percent Pd/C / methanol / 3 h / Ambient temperature 4: 90 percent / CH2Cl2 / 48 h / Ambient temperature 5: 1.) sodium hydride, DMSO, triphenylmethane / 1.) RT, 2.) 10 min 6: 86 percent / 10percent KOH / 1.5 h / Heating View Scheme

1: 98.3 percent / NaH / tetrahydrofuran / -30 deg C to RT, reflux 2: 87 percent / H2 / 10 percent Pd/C / ethanol / Ambient temperature View Scheme

1: 78 percent / AcOH / diethyl ether / 1 h / Heating 2: 1.) CH3CN, 20 deg C, 20 h, 2.) MeOH 3: Zn, AcOH / 20 °C View Scheme

acetic acid; zinc T=20°C; Yield given. Yields of byproduct given;