Multi-step reaction with 11 steps
1: 100 percent / (i-Pr)2NEt / CH2Cl2 / Ambient temperature
2: H2 / 10percent Pd/C / dimethylformamide / 0.25 h / 760 Torr / Ambient temperature
3: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 min
4: 92.3 percent / EtSH, BF3*OEt2 / CH2Cl2 / 1.) -78 deg C, 20 min, 2.) from -78 deg C to -20 deg C , 30 min
5: 85.5 percent / Cp2HfCl2, AgClO4, molecular sieves 4A / CH2Cl2 / 0.83 h / -78 - 0 °C
6: 100 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature
7: 96.2 percent / 3 N aq. NaOH / methanol / Ambient temperature
8: 96.4 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
10: 4-(dimethylamino)pyridine (4-DMAP), pyridine / Ambient temperature
11: cerium(IV) ammonium nitrate (CAN) / acetonitrile; H2O / 0.25 h / -17 °C
With
pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; bis(cyclopentadienyl)hafnium dichloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; silver perchlorate; sodium hydride; N-ethyl-N,N-diisopropylamine; ethanethiol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00018a041