Multi-step reaction with 7 steps
1: 100 percent / LiBr, n-Bu3PO / xylene / 2 h / Heating
2: 100 percent / sodium methoxide / methanol / 2 h / Ambient temperature
3: 74 percent / pyridine / 15 °C
4: 93 percent / 18-crown-6, sodium azide / dimethylformamide / 5 h / 70 °C
5: 60 percent / Et3N, propane-1,3-dithiol / 1) 40 deg C, 1 h, 2) 50 deg C, 1 h, 3) r.t., 18 h
6: 84 percent / NaOH / H2O; tetrahydrofuran / 0 - 5 °C
7: 35 percent / 85percent m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / -30 °C
With
pyridine; 1.3-propanedithiol; sodium hydroxide; sodium azide; 18-crown-6 ether; Tributylphosphine oxide; sodium methylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; xylene;
DOI:10.1021/jm00128a003