Multi-step reaction with 13 steps
1: 94 percent / diethyl ether / 0.17 h / Heating
2: 98 percent / glacial HOAc / 2 h / Heating
3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr
4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C
5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min
6: NaBH4 / methanol / 0.2 h / 0 °C
7: 87 percent / PBr3, pyridine / benzene / 3 h
8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C
9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h
10: 41 percent / BF3 / nitromethane / 2 h / -30 °C
12: 91 percent / m-CPBA / CH2Cl2 / 1 h / -78 °C
13: 82 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature
With
pyridine; sodium tetrahydroborate; 18-crown-6 ether; boron trifluoride; hydrogen; phosphorus tribromide; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; potassium bromide; lithium diisopropyl amide;
palladium on activated charcoal;
In
methanol; diethyl ether; nitromethane; dichloromethane; acetonitrile; benzene;