Multi-step reaction with 13 steps
1: 94 percent / imidazole / dimethylformamide / 1 h / Ambient temperature
2: 65 percent / CH3ONa / methanol / 1.33 h / Ambient temperature
3: 90 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature
4: 94 percent / DIBAL / toluene / 0.75 h / -70 °C
5: 1.) t-BuOK / 1.) THF, 5 deg C, 15 min, 2.) THF, 5 deg C, 60 min
6: K2CO3 / acetone / 15 h / Ambient temperature
7: 90 percent / 4-dimethylpyridine, pyridine / 1.) diminished temp., 10 min, 2.) r.t., 60 min
8: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 10 °C
9: 96 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature
10: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -75 deg C, 1 h, 2.) -75 deg C to r.t.
12: 85 percent / Collins reagent / CH2Cl2 / 2 h / Ambient temperature
13: HCl / tetrahydrofuran / 0.5 h / Ambient temperature
With
pyridine; 1H-imidazole; hydrogenchloride; 4-dimethylpyridine; oxalyl dichloride; Collins oxidation agent; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1135/cccc19971325