Multi-step reaction with 6 steps
1: 1.) lithium tetramethylpiperidide (LiTMP), HMPA / 1.) THF, hexane, from -40 deg C to RT, 2 h, 2.) THF, hexane, a) -15 deg C, b) RT, 8 h
2: 69 percent / MCPBA / CH2Cl2 / 0.5 h / 0 °C
3: 91 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 0.5 h
4: 93 percent / pyridine / 0.5 h
5: 1.) n-BuLi / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 16 h
6: 69 percent / aq. H2SO4 / tetrahydrofuran / 1 h
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sulfuric acid; 2,2,6,6-tetramethylpiperidinyl-lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1080/00397919208021662