Multi-step reaction with 7 steps
1: 1.) n-butyllithium / 1.) THF, hexane, 1 h, 2.) hexane, THF, 30 min
2: 1.) 9-BBN, 2.) aq. 6N NaOH, H2O2 / 1.) THF, RT, 2 h, 2.) THF, H2O, RT, 1 h
3: triethylamine / CH2Cl2
4: NaI / acetone / Heating
5: tributyltin hydride, AIBN / benzene / Heating
6: 94 percent / N,N-diisopropylethylamine / hexane / Ambient temperature
7: 76 percent / 2-methyl-propan-2-ol / 160 °C
With
sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide;
In
hexane; dichloromethane; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jm00037a012