Multi-step reaction with 9 steps
1: 82 percent / aq. CeCl3, NaBH4 / methanol; tetrahydrofuran / 0.5 h / Ambient temperature
2: 81 percent / nBu4NF / tetrahydrofuran / 24 h / Ambient temperature
3: 87 percent / CrO3, pyridine / CH2Cl2 / 1 h / Ambient temperature
4: methanolic KOH / tetrahydrofuran / 1 h / 4 °C
5: 82 percent / H2 / 10 percent Pd/C / methanol / 1.5 h / 760 Torr
6: 1.) aq. CeCl3, NaBH4, 2.) diisopropylethylamine / 1.) MeOH, THF, RT, 0.5 h, 2.) CH2Cl2, RT, 2 h
7: 75 percent / methanolic KOH / 3 h / 50 °C
8: 88 percent / CrO3, pyridine / CH2Cl2 / 0.75 h / Ambient temperature
9: 62 percent / tetrahydrofuran; diethyl ether / 48 h / Ambient temperature
With
pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jm990064o