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: 81 percent / 10percent aq. NaOH / ethanol / 14 h / Heating
7: 49 percent / manganese dioxide / tetrahydrofuran / 120 h / 25 °C
8: 26 percent / ammonia, sodium cyanide, manganese dioxide / propan-2-ol / 65 h / 25 °C
With
hydrogenchloride; sodium cyanide; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; ammonia; sodium methylate; acetyl chloride; dibenzoyl peroxide;
In
tetrahydrofuran; tetrachloromethane; ethanol; isopropyl alcohol;
DOI:10.1021/jm00112a031