Multi-step reaction with 9 steps
1: 90 percent / H2 / PtO2 / ethanol / 50 h / 3102.9 Torr
2: 77 percent / ethane-1,2-diol / 6 h / 110 °C
3: NaOH / ethanol; H2O / 1 h / 80 °C
4: imidazole / dimethylformamide / 5 h / Ambient temperature
5: 90 percent / NaOH, H2O / tetrahydrofuran / 2 h / 0 °C
6: potassium tert-butoxide, oxalyl chloride / methanol; benzene / 0.5 h
7: 1.) sodium azide; / 1.) acetone, 0 deg C, 90 min.; 2.) reflux, 4h
8: 62 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / Ambient temperature
9: CH2Cl2; triethylamine / 1 h / Ambient temperature
With
1H-imidazole; sodium hydroxide; sodium azide; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethylene glycol; triethylamine; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00160a008