Multi-step reaction with 11 steps
1: 1.) NaH / 1.) DMSO, THF, RT, 90 min, 2.) DMSO, THF, RT, overnight
2: 57 percent / H2 / 10percent Pd(OH)2/C / ethyl acetate; methanol / 16 h / Ambient temperature
3: oxalyl chloride/DMSO / CH2Cl2 / 0.75 h / -78 °C
4: Amberlyst-15 / 24 h / Ambient temperature
5: RuCl3*3H2O, NaIO4 / CCl4; acetonitrile; H2O / 2 h / Ambient temperature
6: ethanol; diethyl ether
7: DIBAH / diethyl ether; hexane / 0.75 h / -78 °C
8: diethyl ether; hexane; tetrahydrofuran / 1 h / 0 °C
9: 1.) NaH / 1.) THF, RT, 60 min, 2.) THF, RT, 90 min
10: 1.) BH3*THF, 2.) 1.0 N aq. NaOH, 30percent aq. H2O2 / 1.) THF, 0 deg C, 2.5 h, 2.) THF, RT, 90 min
11: 1.) KH / 1.) THF, from 0 deg C to RT, 95 min, 2.) THF, 30 min, RT
With
ruthenium trichloride; sodium hydroxide; sodium periodate; amberlyst-15; borane-THF; oxalyl dichloride; hydrogen; dihydrogen peroxide; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide;
palladium dihydroxide;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile;