Multi-step reaction with 10 steps
1: 1.) NaOEt / 1.) EtOH, 2.) EtOH, 3 h, reflux
2: H2, ethanolic HCl / PtO2 / 12 h / 20 - 26 °C / 2068.6 - 2585.7 Torr
3: toluene / 2 h / Heating
4: 1.) Me3OBF4, 2.) NaBH4 / 1.) CH2Cl2, 24 h, room temperature, 2.) EtOH, 12 h, 23 deg C
5: 94 percent / H2 / 10percent Pd/C / ethanol; H2O / 24 h / 20 - 26 °C / 2068.6 - 2585.7 Torr
7: 55 percent / SeO2 / chlorobenzene / 1.17 h / 100 °C
8: 85 percent / 16 h / Ambient temperature
9: K2CO3, MeOH / 22 h / Ambient temperature
10: 70 percent / pivalic acid / bis-(2-methoxy-ethyl) ether / 1.) 8 h, 165 deg C, 2.) 16 h, reflux
With
hydrogenchloride; methanol; sodium tetrahydroborate; selenium(IV) oxide; hydrogen; sodium ethanolate; trimethoxonium tetrafluoroborate; potassium carbonate; Trimethylacetic acid;
platinum(IV) oxide; palladium on activated charcoal;
In
ethanol; diethylene glycol dimethyl ether; water; chlorobenzene; toluene;
DOI:10.1021/jo00338a003