Multi-step reaction with 9 steps
1: 75 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
2: 17 percent / polyphosphoric acid / 2 h / 90 °C
3: 1.) NaH / 1.) toluene, 0 deg C, 1 h, 2.) toluene, reflux, 4 h
4: 23 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 6 h / 50 °C
5: 59 percent / H2, AcOH / PtO2
6: 59 percent / NaOMe / methanol / 2.67 h / Heating
7: 1.) Et3N, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 2.) aq. NH4OH / 1.) CH3CN, RT, 45 min, 2.) CH3CN, RT, 30 min
8: BBr3 / CH2Cl2
9: 1.) NaH / 1.) DMF, RT, 60 min, 2.) DMF from 0 deg C to RT
With
ammonium hydroxide; N-Bromosuccinimide; Perbenzoic acid; PPA; hydrogen; sodium methylate; boron tribromide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine;
platinum(IV) oxide; palladium on activated charcoal;
In
methanol; tetrachloromethane; dichloromethane;
DOI:10.1021/jm960395q