Multi-step reaction with 18 steps
1: 97 percent / diisopropylethylamine / CH2Cl2
2: 71 percent / NaOH / 72 h / 80 °C
3: 97 percent / dichlorodicyanoquinone / CH2Cl2; H2O / 0.33 h
4: 88 percent / aq. NaOH / methanol
5: 77 percent / 1.) DMSO, oxalyl chloride, 2.) triethylamine / CH2Cl2 / -50 °C
6: 95 percent / benzene / 4 h / 80 °C
7: 92 percent / diisopropylethylamine / CH2Cl2 / 48 h / Heating
8: 1.) 9-borabicyclo<3.3.1>nonane, 2.) NaOH, H2O2 / 1.) THF, reflux, 1.5 h, 2.) 1 h
9: 80 percent / H2 / Pd/C / methanol
10: 78 percent / 1.) DMSO, oxalyl chloride, 2.) triethylamine / CH2Cl2 / -50 °C
11: 2.) b) hexamethylphosphoramide / 2.) a) THF, -70 deg C, 1 h, b) 3 h
12: 1.) NaOH, / 1.) H2O, EtOH, 6 h, 2.) THF, 16 h
13: 2.) THF, from -72 deg C to RT, 3h
14: 81 percent / LiN(SiMe3)2 / 2.5 h / -72 °C
15: H2O2, m-chloroperbenzoic acid / 0.42 h / -50 - 0 °C
16: toluene / 16 h / 80 °C
17: 89 percent / aq. NaOH / methanol / 2.5 h
18: 55 percent / aq. HF / acetonitrile / 6 h
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; hydrogen fluoride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
methanol; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1039/c39900000467