Multi-step reaction with 10 steps
1: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) THF, hexane, from -70 deg C to room temp., 18 h
2: 91 percent / NaBH4 / 20 h / Ambient temperature
3: 29 percent / p-TsOH / toluene / 0.03 h / Heating
4: 36 percent / DDQ / benzene / 0.5 h
5: 31 percent / NaOEt, butyl nitrite / ethanol / Ambient temperature
6: 55 percent / formic acid, zinc / ethanol; H2O / a) 0 deg C, 3 h, b) room temp., overnight
7: 2.22 N NaOH / ethanol
8: 87 percent / Et3N / ethanol; H2O; dioxane
9: 100 mg / N-(ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline (EEDQ) / tetrahydrofuran; acetonitrile / 5.5 h / Ambient temperature
10: 73 percent / p-toluenesulfonic acid, NaHCO3 / acetonitrile / 0.5 h / Ambient temperature
With
sodium hydroxide; sodium tetrahydroborate; n-butyllithium; formic acid; n-Butyl nitrite; sodium ethanolate; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc;
In
tetrahydrofuran; 1,4-dioxane; ethanol; water; toluene; acetonitrile; benzene;
DOI:10.1021/jm00150a023