Multi-step reaction with 9 steps
1: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, RT, 72 h
2: 26 percent / HBr, AcOH / CH2Cl2 / 18 h / Ambient temperature
3: CH2Cl2 / 2 h / Ambient temperature
4: PdCl2(Ph3P)2, LiCl / dimethylformamide / 12 h / Ambient temperature
5: 1.) 9-BBN, 2.) 1 N aq. NaOH, 30percent H2O2 / 1.) THF, RT, 12 h, 2.) THF, 30 min
6: CrO3, H2SO4 / acetone / 0 °C
7: CH2Cl2 / 1 h / Ambient temperature
8: CH2Cl2 / 24 h / Ambient temperature
9: aq. LiOH / methanol; tetrahydrofuran / 48 h
With
chromium(VI) oxide; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; sulfuric acid; hydrogen bromide; dihydrogen peroxide; sodium hydride; acetic acid; lithium chloride;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm9506985