Multi-step reaction with 12 steps
1: 1.) NaH / 1.) THF, 45 min, RT, 2.) THF, 45 min
2: 85 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -70 °C
3: 1.) nBuLi / 1.) THF, hexane, 30 min, 2.) THF, hexane, a) -25 deg C, 30 min, b) 1 h, RT
4: 1.) 9-BBN, 2.) aq. H2O2, NaOH / 1.) THF, RT, 1 h, 2.) EtOH, 15 min
5: 78 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -70 °C
6: 1.) nBuLi / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, 1 h
7: methanol; diethyl ether / 0.17 h / Ambient temperature
8: 73 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
9: 96 percent / pyridine / 1 h / Ambient temperature
10: dimethylsulfoxide / 5 h / 90 - 100 °C
11: 59 percent / NH2NH2 / CH2Cl2; ethanol / 24 h / Ambient temperature
12: 40 percent / Et3N / CH2Cl2 / 3 h / 0 °C
With
pyridine; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; triethylamine; hydrazine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/0223-5234(96)88240-7