Multi-step reaction with 11 steps
1: 80 percent / Me2S*BH3 / 1,2-dimethoxy-ethane / 3 h / Heating
2: 46 percent / DBU / tetrahydrofuran
3: 73 percent / pyridinium dichromate (PDC) / CH2Cl2
4: 99 percent / aq. HCl / dioxane / 2 h / Heating
5: oxalyl chloride / benzene; dimethylformamide / 0.5 h
6: aq. Na2CO3 / tetrahydrofuran / 1 h / Ambient temperature
7: 1.) AcONa / ethanol / 0.5 h
8: NaBH3CN / ethanol / 3 h
9: cyclohexadiene / 10percent Pd/C / ethanol / 48 h / Heating
10: 2.) conc. aq. NH3 / 1.) EtOH, RT, 24 h 2.) EtOH
11: 91 percent / m-chloroperbenzoic acid (m-CPBA) / CHCl3 / -10 - 20 °C
With
hydrogenchloride; ammonium hydroxide; dipyridinium dichromate; oxalyl dichloride; dimethylsulfide borane complex; sodium acetate; sodium cyanoborohydride; sodium carbonate; cyclohexa-1,3-diene; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm00385a012