Multi-step reaction with 8 steps
1: BF3*Et2O / 2 h / Heating
2: powdered KOH / dioxane / 4 h / Heating
3: 1.) KOt-Bu, 2.) 2M HCl / 1.) DMSO, 100 deg C, 3 h, 2.) acetone, reflux, 30 min
4: SOCl2 / toluene; CHCl3 / 0.5 h / 20 °C
5: 1.) Bu3SnLi, 2.) BuLi / 1.) THF, -78 deg C, 1.5 h, 2.) THF/hexane, -78 deg C -> -65 deg C, 15 min
6: tetrahydrofuran / 1 h
7: 90 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, 1-hydroxybenzotriazol, (i-Pr)2EtN / various solvent(s) / 1 h / Ambient temperature
8: 75 percent / CF3COOH / CH2Cl2 / 2 h / Ambient temperature
With
hydrogenchloride; potassium hydroxide; n-butyllithium; thionyl chloride; tri-n-butyltin lithium; boron trifluoride diethyl etherate; potassium tert-butylate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; toluene;
DOI:10.1002/hlca.19960790602