Multi-step reaction with 9 steps
1: 90 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 2.5 h / Ambient temperature
2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, MeOH, pyridine, -78 deg C, 2.) 25 deg C, 16h
3: 1.) Zn, Ph3P / 1.) CH2Cl2, 25 deg C, 24 h, 2.) 25 deg C, 2 h
4: 1.) n-BuLi / 1.) THF, hexane, -78 to -20 deg C; -20 deg C, 1 h, 2.) 0 deg C, 2 h
5: 1.) Cp2ZrHCl, 2.) I2 / 1.) CH2Cl2, 25 deg C, 90 min, 2.) CCl4, 0 deg C
6: 57 percent / CrCl2, NiCl2 / dimethylsulfoxide / 72 h / 25 °C
7: 98 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / 0 °C
8: 97 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C
9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) 0 deg C, 3 h
With
2,6-dimethylpyridine; chromium dichloride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; dimethylsulfide; iodine; sodium hexamethyldisilazane; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; nickel dichloride; zinc;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;