Multi-step reaction with 8 steps
1: LiOH*H2O / methanol / 72 h / Ambient temperature
2: copper-bronze, quinoline / 1 h / Heating
3: 98 percent / hydroquinone / CH2Cl2 / 312 h / 9050090 Torr
4: 1) 1 M aq. KOH, 2) 37percent aq. formaldehyde / 1) THF, water, r.t., 45 min, 2) 20 min
5: 95 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C
6: 96 percent / imidazole / dimethylformamide / 16 h / Ambient temperature
7: 1) borane-THF complex, 2) 5 M aq. NaOH, 30percent H2O2 / 1) THF, 0 deg C, 1 h, then r.t., 1 h, 2) reflux, 30 min
8: 89 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine N-oxide, molecular sieves (3 Angstroem) / acetonitrile / 20 h / Ambient temperature
With
1H-imidazole; quinoline; potassium hydroxide; lithium hydroxide; sodium hydroxide; formaldehyd; tetrapropylammonium perruthennate; borane-THF; 3 A molecular sieve; dihydrogen peroxide; copper; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; hydroquinone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00042a036