Multi-step reaction with 9 steps
1: 83.4 percent / H2 / 10percent Pd/C / benzene; heptane / 30 h / 2585.7 Torr / Ambient temperature
2: 100 percent / BF3*Et2O / CH2Cl2 / 0.5 h / Ambient temperature
3: 96 percent / TsOH / benzene / 0.58 h / Heating
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) CH2Cl2, from -60 deg C to 0 deg C
5: 93 percent / collidine / CH2Cl2 / 0.17 h
6: 1.) O3, Py, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, from -78 deg C to RT
7: aq. NaIO4 / tetrahydrofuran / 0.17 h / Ambient temperature
8: diethyl ether / 0.08 h / 0 °C
9: 97 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
With
pyridine; 2,3,5-trimethyl-pyridine; hydrogenchloride; sodium periodate; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; benzene;
DOI:10.1016/0040-4020(96)00735-1