Multi-step reaction with 11 steps
1: 90 percent / m-CPBA, disodium phosphate, bis(2-tert-butyl-3-hydroxy-4-methylphenyl)sulphide / CH2Cl2 / 8 h / Heating
2: 100 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating
3: 100 percent / BIO-RAD AG50W-X2 50-100 mesh H+ ion exchange resin / methanol / 2 h / Heating
4: 88 percent / HIO4 / pyridine; H2O / 0.33 h / Ambient temperature
5: 84 percent / 2,6-dimethylpyridine / CH2Cl2 / 0.08 h / -5 °C
6: 99 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / Ambient temperature
7: 80 percent / Et3N / palladium(II)acetate, triphenylphosphine / dimethylformamide
8: 87 percent / m-CPBA, disodium phosphate, bis(2-tert-butyl-3-hydroxy-4-methylphenyl)sulphide / CH2Cl2 / 8 h / Heating
9: 96 percent / LiAlH4 / tetrahydrofuran / Heating
10: 98 percent / DMAP, pyridine / CH2Cl2 / 0.5 h
11: 86 percent / 48percent hydrofluoric acid / CH2Cl2; acetonitrile / a) -5 deg C, 5 min, b) room temp., 15 min
With
pyridine; 2,6-dimethylpyridine; dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; bis(2-tert-butyl-3-hydroxy-4-methylphenyl)sulphide; BIO-RAD AG50W-X2 50-100 mesh H+ ion exchange resin; hydrogen fluoride; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium diacetate; triphenylphosphine;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;