Multi-step reaction with 10 steps
1: 88 percent / diethyl ether / 0.5 h / Ambient temperature
2: 96 percent / imidazole / dimethylformamide / 30 °C
3: 1) O3; 2) Et3N / 1) CH2Cl2, -78 deg C; 2) RT, 4 h, CH2Cl2
4: 82 percent / tetrahydrofuran / 1.5 h / -78 °C
5: 91 percent / Et3N, 4-N,N-dimethylaminopyridine / CH2Cl2 / Ambient temperature
6: 92 percent / n-Bu4NF, NH4Cl / tetrahydrofuran / 24 h / Ambient temperature
7: 100 percent / (Me3Si)2NH, n-Buli / tetrahydrofuran / 15 h / Ambient temperature
8: 73 percent / n-Bu3SnH, azoisobutyronitrile / benzene / 1 h / Heating
9: 85 percent / H2 / Raney Ni / ethyl acetate / 5 h / Heating
10: 80 percent / pyridinium chlorochromtate, NaOAc / CH2Cl2 / Ambient temperature
With
1H-imidazole; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium acetate; ammonium chloride; ozone; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; pyridinium chlorochromate;
nickel;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1039/C39870001002