Multi-step reaction with 10 steps
1: 1.) NaH / 1.) DMF, 20 deg C, 10 min; 2.) DMF, 20 deg C, 2 h
2: 85 percent / 5percent Pd/C, H2 / ethyl acetate / 6 h / 3750.3 Torr
3: 84 percent / NaNO2, 50percent H3PO2 / H2O / 2 h, 0 deg C, 5 h, 20 deg C
4: 81 percent / AlCl3 / benzene / 15 h / Heating
5: 81 percent / Na2CO3 / ethanol; H2O / 5 h / 20 °C
6: NBS, AIBN / CCl4 / 2 h / Heating
7: toluene / 15 h / 100 °C
8: 89 percent / K2CO3, 18-crown-6 / CH2Cl2 / 24 h / Heating
9: 94 percent / 5percent Pd/C, H2, triethylamine / ethyl acetate / 12 h / 3750.3 Torr
10: 1.) LiAlH4; 2.) satd. NH4Cl / 1.) diethyl ether, 5 h, reflux
With
palladium on activated charcoal; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); hydrogen; hypophosphorous acid; sodium hydride; sodium carbonate; potassium carbonate; ammonium chloride; triethylamine; sodium nitrite;
In
tetrachloromethane; ethanol; dichloromethane; water; ethyl acetate; toluene; benzene;
DOI:10.1002/(SICI)1099-0690(199805)1998:5<877::AID-EJOC877>3.0.CO;2-S