Multi-step reaction with 10 steps
1: 90 percent / aq. Tl(NO3)3 / methanol; tetrahydrofuran / 0.17 h
2: 89 percent / p-TsOH / dimethylformamide; methanol / 24 h
3: 1.) MCPBA, 2.) silica gel / 1.) benzene, hexanes, 0 deg C - RT, 30 min, 2.) benzene, hexanes, 40 min
4: 59 percent / NaBH4 / methanol / 0.33 h / 0 °C
5: 91 percent / imidazole / dimethylformamide / 2 h
6: 98 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
7: 81 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C
8: 4 percent / 18-crown-6 / dimethylformamide / 16 h / 45 °C
9: 70 percent / Hg(OCOCF3)2, Et3N / 20 h / Ambient temperature
10: 25 percent / xylene / 14 h / 210 °C
With
1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 18-crown-6 ether; mercury(II) trifluoroacetate; silica gel; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; thallium(III) nitrate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; xylene;
DOI:10.1021/ja00087a023