ammonium formate; palladium on activated charcoal in methanol 0.75 h; Ambient temperature;

1: 1) NaOMe 2) 30percentH2O2, 10N NaOH / 1) ether, 10h, reflux 2: SOCl2 / toluene; dimethylformamide / 1) r.t., overnight 2) 50 deg C 3: 1) NaH / 1) THF 2) toluene, DMF, overnight 4: 75 percent / NH4OH / methanol / 0.75 h / Ambient temperature 5: 90 percent / ammonium formate / 10percent Pd/C / methanol / 0.75 h / Ambient temperature View Scheme

1: 1) NaH / 1) THF 2) toluene, DMF, overnight 2: 75 percent / NH4OH / methanol / 0.75 h / Ambient temperature 3: 90 percent / ammonium formate / 10percent Pd/C / methanol / 0.75 h / Ambient temperature View Scheme

1: SOCl2 / toluene; dimethylformamide / 1) r.t., overnight 2) 50 deg C 2: 1) NaH / 1) THF 2) toluene, DMF, overnight 3: 75 percent / NH4OH / methanol / 0.75 h / Ambient temperature 4: 90 percent / ammonium formate / 10percent Pd/C / methanol / 0.75 h / Ambient temperature View Scheme

1: 75 percent / NH4OH / methanol / 0.75 h / Ambient temperature 2: 90 percent / ammonium formate / 10percent Pd/C / methanol / 0.75 h / Ambient temperature View Scheme