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: sodium azide / dimethylsulfoxide / 16 h / 25 °C
8: H2 / 10percent Pd/C / methanol / 1 h / 25 °C / 760 Torr
9: 75 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, dicyclohexylcarbodiimide / 96 h / 0 °C
10: 1.68 g / anisole, trifluoroacetic acid / tetrahydrofuran; H2O / 7 h / 25 °C
With
hydrogenchloride; N-Bromosuccinimide; thionyl chloride; sodium azide; hydrogen; sodium methylate; benzotriazol-1-ol; methoxybenzene; acetyl chloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; dibenzoyl peroxide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; chloroform; water; dimethyl sulfoxide;
DOI:10.1021/jm00112a031