Multi-step reaction with 9 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: 1.) MgSO4, 2.) NaBH4 / 1.) CH2Cl2, 0 deg C, 2 h, 2.) CH3OH, 0 deg C, 30 min
5: aq. NaHCO3 / CH2Cl2 / 8 h / Ambient temperature
6: (n-Bu)4NF / tetrahydrofuran / 0.33 h / Ambient temperature
7: m-CPBA / CH2Cl2 / 1.5 h / 0 °C
8: diisopropylamine / CH2Cl2 / 20 h / Heating
9: Ag2O / CDCl3 / 2 h / Ambient temperature
With
1H-imidazole; sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; borane-THF; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydrogencarbonate; magnesium sulfate; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide;
In
tetrahydrofuran; chloroform-d1; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00100a039