Multi-step reaction with 13 steps
1: piperidine / ethanol / 3 h / Heating
2: 1 N aq. (NH4)2Ce(NO3)6 / acetone / 0.33 h / 0 °C
3: 98.3 percent / m-chloroperoxybenzoic acid / CHCl3 / 4 h / Ambient temperature
4: POCl3 / 2 h / Heating
5: LiAlH4 / tetrahydrofuran / 2 h / 20 °C
6: MnO2 / CHCl3 / 5 h / Heating
7: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 1.5 h
8: SOCl2 / 0.5 h / 60 °C
9: Zn, AcOH / 0.58 h / Ambient temperature
10: 93.1 percent / POCl3, pyridine / 3 h / 100 °C
11: 73.7 percent / m-chloroperoxybenzoic acid / CHCl3 / 4 h / Ambient temperature
12: 44.3 percent / AcOH / 2 h / 120 °C
13: 94.1 percent / 10percent aq. K2CO3 / methanol / 1.5 h
With
piperidine; pyridine; manganese(IV) oxide; lithium aluminium tetrahydride; thionyl chloride; ammonium cerium(IV) nitrate; potassium carbonate; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; zinc; trichlorophosphate;
In
tetrahydrofuran; methanol; ethanol; chloroform; acetone;
DOI:10.1248/cpb.42.1841