Multi-step reaction with 9 steps
1: tetrahydrofuran / 2 h / 20 °C
2: 88 percent / 4.5 N aq. HCl / 12 h / Heating
3: oxalyl chloride / CH2Cl2 / 3 h / 25 °C
4: tetrahydrofuran / 1 h / 25 °C
5: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
6: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
7: 1.) n-BuLi, t-butyl alcohol / 1.) THF, 0 deg C, 2.) 25 deg C, 16 h
8: 1.) cadimium, 2.) hexamethylphosphoric triamide, copper(I) bromide / 1.) DMF, 25 deg C, 2 h, 2.) DMF, 70-75 deg C, 6 h
9: 80 percent / 1.5 M tetrafluoroboric acid / acetonitrile / 18 h / 25 °C
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; tetrafluoroboric acid; n-butyllithium; oxalyl dichloride; sodium methylate; copper(I) bromide; cadmium; tert-butyl alcohol; dibenzoyl peroxide;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; acetonitrile;
DOI:10.1021/jm00112a031