Multi-step reaction with 6 steps
1: 1.) p-toluenesulfonic acid, 2.) CrO3, 3,5-dimethylpyrazole / 1.) 83 deg C, 7.5 h, 2.) CH2Cl2, -23 deg C, 2.5 h
2: 82 percent / H2 / 10 percent Pd/C / methanol / 1.5 h / 760 Torr
3: 1.) aq. CeCl3, NaBH4, 2.) diisopropylethylamine / 1.) MeOH, THF, RT, 0.5 h, 2.) CH2Cl2, RT, 2 h
4: 75 percent / methanolic KOH / 3 h / 50 °C
5: 88 percent / CrO3, pyridine / CH2Cl2 / 0.75 h / Ambient temperature
6: 62 percent / tetrahydrofuran; diethyl ether / 48 h / Ambient temperature
With
pyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; hydrogen; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jm990064o