Multi-step reaction with 8 steps
1: 86 percent / imidazole / dimethylformamide / 4 h / Ambient temperature
2: 1.) BH3*THF, 2.) 30percent H2O2, 3 N NaOH / 1.) THF, 0 deg C, 10 min; 2 h, 2.) 0 deg C, 15 min; 1 h
3: 58 percent / PDC / CH2Cl2 / 20 h / Ambient temperature
4: 83 percent / t-BuLi / tetrahydrofuran; pentane / 1.) -78 deg C, 1 h, 2.) -78 deg C, 30 min; r.t., 30 min
5: 2 N NaOH / tetrahydrofuran; ethanol / 48 h / Ambient temperature
6: 94 percent / hexamethyldisilazane, pyridine / 3 h / Ambient temperature
7: (n-Bu)4NF / tetrahydrofuran; CDCl3 / 0.08 h
8: Ag2O / CDCl3 / 0.17 h / Ambient temperature
With
pyridine; 1H-imidazole; sodium hydroxide; dipyridinium dichromate; borane-THF; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; 1,1,1,3,3,3-hexamethyl-disilazane; silver(l) oxide;
In
tetrahydrofuran; chloroform-d1; ethanol; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo00100a039