Multi-step reaction with 18 steps
1: trifluoroacetic acid / tetrahydrofuran; H2O / 40 h / Ambient temperature
2: Pb(OAc)4 / benzene / 0.25 h / Ambient temperature
3: 88.9 percent / 1,2-dichloro-ethane / 17 h / Heating
4: 90.4 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
5: 76.2 percent / m-chloroperbenzoic acid / CH2Cl2 / 2.5 h / -5 °C
6: 86.6 percent / H2, NaHCO3 / 10 percent Pd-C / ethanol / 5 h / Ambient temperature
7: 69.3 percent / DDQ / CH2Cl2 / 0.42 h / 16 °C
8: 72 percent / AlH3 / diethyl ether / 1 h / Ambient temperature
9: 95 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature
10: 94 percent / TsOH / acetone / 30 h / Ambient temperature
11: 100 percent / 1M KOH / methanol / 1 h / Ambient temperature
12: 91 percent / pyridinium chlorochromate, molecular sieves 3 Angstroem / CH2Cl2 / 0.25 h / Ambient temperature
13: 1,2-dichloro-ethane / 12 h / Heating
14: 99.7 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
15: 97.7 percent / m-CPBA / CH2Cl2 / 2.5 h / -15 - -10 °C
16: 92 percent / Et3N / benzene / 0.03 h / Ambient temperature
17: 97.6 percent / NaI / methanol / 1 h / Heating
18: 96 percent / Zn-Cu couple / ethanol / 0.33 h / Heating
With
pyridine; aluminium hydride; lead(IV) acetate; potassium hydroxide; lithium aluminium tetrahydride; 3 A molecular sieve; hydrogen; copper; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; zinc;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; benzene;