Multi-step reaction with 10 steps
1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, from -78 deg C to 0 deg C
2: 58 percent / AlCl3, tert-butylamine-borane / toluene / 2 h / 5 °C
3: 99 percent / trifluoroacetic acid, triethylsilane / 1.) 5 deg C, 60 min, 2.) RT, 18 h
4: 98 percent / ethanethiol, lithium hydride / dimethylformamide / 3 h / Heating
5: 82 percent / K2CO3 / acetone / 18 h / Heating
6: 69.5 percent / 1,2-dichloro-benzene / 21 h / Heating
7: K2CO3 / butan-2-one / 22 h / Heating
8: 1.) BH3*THF, 2.) a) 30percent aq. H2O2, 1 N aq. NaOH, b) NaS / 1.) 0 deg C, 75 min, 2.) a) THF, methanol, 30 min, b) H2O
9: CBr4, triphenylphosphine / CH2Cl2 / 0.75 h
10: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 18 h
With
triethylsilane; sodium hydroxide; n-butyllithium; aluminium trichloride; borane-THF; carbon tetrabromide; dihydrogen peroxide; lithium hydride; sodium hydride; borane tert-butylamine; potassium carbonate; triphenylphosphine; trifluoroacetic acid; ethanethiol;
In
dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; toluene; butanone;
DOI:10.1021/jm00085a019