sodium hydroxide; hydrogen; palladium on activated carbon in ethyl acetate Product distribution / selectivity;

potassium carbonate in methanol 6 h; Ambient temperature;

potassium carbonate in methanol T=20°C; 1 h;

1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature View Scheme

1: 1.) NaH, 2.) n-BuLi 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 4: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 5: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature View Scheme

1: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 2: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 3: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature View Scheme

1: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 2: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h 2: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C 3: 65 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h 4: 83.6 percent / K2CO3 / methanol / 6 h / Ambient temperature View Scheme

diisobutylaluminium hydride in tetrahydrofuran; toluene T=-80 - -72°C; 1 h;

1: 83 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C 2: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h View Scheme