Multi-step reaction with 8 steps
1: tetrahydrofuran / 2 h / 20 °C
2: 88 percent / 4.5 N aq. HCl / 12 h / Heating
3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h
4: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
6: 1.) n-BuLi, t-butyl alcohol / 1.) THF, 0 deg C, 2.) 25 deg C, 16 h
7: 80 percent / potassium methanethiolate / dimethylformamide / 4 h / 125 °C
8: 1.) oxalyl chloride, N-methylmorpholine / 1.) chloroform, DMF, -20 deg C, 0.35 h, 2.) a) 25 deg C, 4 h, b) reflux, 40 h
With
4-methyl-morpholine; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; sodium methylate; potassium methanethiolate; acetyl chloride; tert-butyl alcohol; dibenzoyl peroxide;
In
tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00112a031