Multi-step reaction with 10 steps
1: 1.) NaNO2, H+, KBr, 2.) CH3CO3H
2: 90 percent / PBu3 / methanol / 0.75 h / Ambient temperature
3: 84.2 percent / Heating
4: 1.) AcOAg, 2.) thiourea, pyridine / 1.) CH2Cl2, 6 h, 2.) DMF, from 0 deg C to RT
5: 1.) oxalyl chloride, DMSO, 2.) TEA / 1.) CH2Cl2, -70 deg C, 3 h, 2.) CH2Cl2, from -70 deg C to -10 deg C, 20 min
6: 13 percent / LiClO4 / acetonitrile / 4 h / -20 °C
7: 32 percent / DIBAH / toluene / 6 h / Ambient temperature
8: 77 percent / tetrahydrofuran / 3 h
9: aq. NaIO4, RuO2 hydrate, NaHCO3 / acetonitrile; CH2Cl2 / 0.5 h / Ambient temperature
10: 78 percent / aq. NaHCO3 / tetrahydrofuran; methanol / 24 h
With
pyridine; peracetic acid; ruthenium(IV) oxide; sodium periodate; oxalyl dichloride; tributylphosphine; TEA; silver(I) acetate; lithium perchlorate; hydrogen cation; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; thiourea; potassium bromide; sodium nitrite;
In
tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jm9601967