Multi-step reaction with 10 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: 90 percent / 1.0 M lithium aluminum hydride / tetrahydrofuran / 2 h / Heating
9: SOCl2 / CHCl3 / 2 h / 25 °C
10: dimethylsulfoxide / 24 h / 25 °C
With
hydrogenchloride; N-Bromosuccinimide; lithium aluminium tetrahydride; thionyl chloride; sodium methylate; sodium; acetyl chloride; dibenzoyl peroxide;
In
tetrahydrofuran; tetrachloromethane; chloroform; dimethyl sulfoxide;
DOI:10.1021/jm00112a031