Multi-step reaction with 8 steps
1: pyridine / Ambient temperature
2: 54 percent / silver fluoride / pyridine / 2.5 h / Ambient temperature
3: 1.) 2 M methanolic NaOMe; 2.) 1 M borane; 3.) 3 M NaOH, H2O2 / 1.) chloroform, 1.5 h, RT; 2.) THF, 1 h, RT; 3.) THF, EtOH, 50 deg C, 2 h
4: 1.) pyridine, 80 deg C, 12 h; 2.) pyridine, 2 h
5: 93 percent / methanolic 2 M BF3*Et2O / CH2Cl2 / 6 h / Ambient temperature
6: 1.) CrO3, 3.5 M H2SO4; 2.) 3 M NaOH / 1.) acetone, 5 h, RT; 2.) 0 deg C, 12 h; 3.) ether
7: 83 percent / silver triflate, 2,4,6-trimethylpyridine / CH2Cl2 / 1.) 15 min, 0 deg C; 2.) 1 h, 0 deg C
8: 1.) 1 M NaOH / 1.) methanol, 3 h, RT; 2.) ether
With
pyridine; 2,4,6-trimethyl-pyridine; chromium(VI) oxide; sodium hydroxide; sulfuric acid; boron trifluoride diethyl etherate; borane; dihydrogen peroxide; sodium methylate; silver trifluoromethanesulfonate; silver fluoride;
In
pyridine; dichloromethane;
DOI:10.1016/0008-6215(88)85095-X