Multi-step reaction with 19 steps
1: 86 percent / aq. HCl / diethyl ether / 3 h / 0 °C
2: 60 percent / O2 / Pt / H2O; ethyl acetate; propan-2-ol / 40 °C
3: 98 percent / K2CO3 / dimethylformamide / 12 h / Ambient temperature
4: pyridine / CH2Cl2 / 1 h
5: LiI*3H2O / tetrahydrofuran; acetic acid / 48 h / Heating
6: 97 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C
7: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature
8: 92 percent / H2 / 10percent Pt/C / ethyl acetate / 15 h / 2068.6 Torr
9: 95 percent / KHMDS / tetrahydrofuran / 0.5 h / -78 °C
10: 86 percent / NaBH4 / propan-2-ol / 3 h / 0 °C
11: 97 percent / Et3N / tetrahydrofuran / 2 h / 0 °C
12: 96 percent / NaH / tetrahydrofuran / 3 h / 0 °C
13: 95 percent / H2 / 5percent Pt/C / ethyl acetate / 5 h
14: 95 percent / LAH / tetrahydrofuran / 2 h / 0 °C
15: 93 percent / diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature
16: 95 percent / Bu4NF / tetrahydrofuran / 10 h
17: 97 percent / Et3N / tetrahydrofuran / 2 h / 0 °C
18: 78 percent / NaH, 2-methoxyethanol / dimethylformamide / 5 h / 0 °C
19: 89 percent / PPTS / 2-methyl-propan-2-ol / 3 h / Heating
With
pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; 2-methoxy-ethanol; tetrabutyl ammonium fluoride; hydrogen; oxygen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium iodide;
platinum on activated charcoal; platinum;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol;
DOI:10.1021/jo00081a019