Multi-step reaction with 15 steps
1: 1.) 15percent n-BuLi; 2.) Hexamethylphosphorsaeuretriamid / 1.) hexan, THF, -78 deg C, 2h; 2.) -73 deg C, 15 min; 3.) -78 deg C, 2h
2: 8 percent / aq. HCl / acetone / 24 h / Ambient temperature
3: 91 percent / 70percent Perchlorsaeure / CH2Cl2 / 0.75 h / Ambient temperature
4: 84 percent / 5percent KOH / methanol / 0.75 h / 0 °C
5: 93 percent / diethyl ether / 1.75 h / -78 °C
6: Spur Sudan III, O3; 2.) Zn / 1.) acetic acid, ethyl acetate, -78 deg C; 2.) RT, 1h
7: 77 percent / m-Chloperbenzoesaeure / CH2Cl2 / 192 h / 50 °C
8: 90 percent / 5percent KOH / methanol / 1 h / 0 °C
9: 80 percent / CrO3, H2SO4 / acetone / 0.08 h / 0 °C
10: 77 percent / Diisopropylethylamin / CH2Cl2 / 48 h / Ambient temperature
11: 97 percent / 5percent KOH / methanol / 3 h / 0 °C
12: 83 percent / CrO3, H2SO4 / acetone / 0.08 h / 0 °C
13: 1.) Diisopropylamin, 15percent n-Butyllithium / 1.) THF, hexan, -78 deg C, 15 min; 2.) -78 deg C, 1h, THF; 3.) 0 deg C 1h, RT, 12h
14: 87 percent / 1percent HCl / tetrahydrofuran; methanol / 30 h / 65 °C
15: 38 percent / 1percent HCl / tetrahydrofuran; methanol / 30 h / 70 °C
With
chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; perchloric acid; sulfuric acid; ozone; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; Sudan III;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;
DOI:10.1016/S0040-4020(01)91500-5