hydrogen; palladium on activated charcoal in methanol T=25°C; P=3040 Torr;

hydrogen; palladium on activated charcoal in methanol; water T=25°C; P=3040 Torr;

1.1: 88 percent / NaH / dimethylformamide / 6.5 h / 20 °C 2.1: O3 / methanol / -78 °C 2.2: Me2S; p-CH3C6H4SO3H / methanol / -78 - 20 °C 2.3: 98 percent / amberlyst-15 / acetone / 20 °C 3.1: 97 percent / H2 / Pd/C / methanol / 25 °C / 3040 Torr View Scheme

1.1: 88 percent / NaH / dimethylformamide / 6.5 h / 20 °C 2.1: O3 / methanol / -78 °C 2.2: Me2S; p-CH3C6H4SO3H / methanol / -78 - 20 °C 2.3: 98 percent / amberlyst-15 / acetone / 20 °C 3.1: 97 percent / H2 / Pd/C / methanol / 25 °C / 3040 Torr View Scheme

1.1: O3 / methanol / -78 °C 1.2: Me2S; p-CH3C6H4SO3H / methanol / -78 - 20 °C 1.3: 98 percent / amberlyst-15 / acetone / 20 °C 2.1: 97 percent / H2 / Pd/C / methanol / 25 °C / 3040 Torr View Scheme

(i) KI, K2CO3, acetone, (ii) H2, Pd-C, EtOH; Multistep reaction;