Multi-step reaction with 9 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: 97 percent / thionyl chloride / CHCl3 / 4 h / 25 °C
7: 4.77 g / Na / 18 h / 25 °C
8: 62 percent / hydrazine / methanol / 120 h / Heating
9: 40 percent / triethylamine / CH2Cl2 / a) -78 deg C, 1 h, b) 25 deg C, 2 h
With
hydrogenchloride; N-Bromosuccinimide; thionyl chloride; sodium methylate; sodium; triethylamine; acetyl chloride; hydrazine; dibenzoyl peroxide;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; chloroform;
DOI:10.1021/jm00112a031