Multi-step reaction with 10 steps
1: 92 percent / imidazole / dimethylformamide / Ambient temperature
2: 64 percent / chromium(VI) oxide, 3,5-dimethylpyrazole / CH2Cl2 / 4.5 h / -20 °C
3: 1.) lithium tri-sec-butylborohydride, 2.) aq. NaOH, 30percent H2O2 / 1.) THF, -78 deg C, 5 h, 2.) THF, RT, 30 min
4: pyridine / 10 h / Ambient temperature
5: tetrabutylammonium fluoride / tetrahydrofuran / 24 h / Ambient temperature
6: chromium(VI) oxide, pyridine, MgSO4 / CH2Cl2 / 3 h / 0 °C
7: pyridine / 60 h / Ambient temperature
8: MeOH / diethyl ether / 0.08 h / 0 °C
9: 76 percent / aq. p-TsOH*H2O / acetone / 120 h / Ambient temperature
10: 1.) aq. NaOH, 2.) MeOH / 1.) THF, MeOH, RT, 5 d, 2.) ether, 0 deg C, 5 min
With
pyridine; 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; methanol; sodium hydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; L-Selectride; magnesium sulfate; toluene-4-sulfonic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0039-128X(98)00047-6