Multi-step reaction with 10 steps
1: 1) H2; 2) H2 / 1) Ranay-Ni W2; 2) 10percent Pd/C / 1.) toluene, ethanol, heating, 5 bar, 80 h; 2) MeOH, 5 bar 120 h
2: 1) NEt3; 2) POCl3 / 1) CH2Cl2; 2) MeCN, reflux
3: 85 percent / LiAlH4/AlMe3 / tetrahydrofuran / 3 h / -78 - 0 °C
4: K2CO3 / propan-1-ol / Heating
5: 47 percent HBr / 9 h / 70 °C
6: 86 percent / NEt3, 4-N,N-dimethylaminopyridine / CH2Cl2
7: 49 percent / Pd(PPh3)2Cl2, NaOAc, N,N-dimethylacetamide / 100 °C
8: 95 percent / LiAlH4 / tetrahydrofuran
9: 1) CCl2Br-CCl2Br/polym. PPh3; 2) LiAlH4 / 1) CH2Cl2; 2) THF
10: H2 / 10 percent Pd/C / methanol
With
dmap; bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; 1,2-dibromo-1,1,2,2-tetrachloroethane; N,N-dimethyl acetamide; polym. PPh3; hydrogen bromide; hydrogen; trimethylaluminum; sodium acetate; potassium carbonate; triethylamine; trichlorophosphate;
palladium on activated charcoal; nickel;
In
tetrahydrofuran; methanol; propan-1-ol; dichloromethane;