Multi-step reaction with 10 steps
1: 1) silver silicate, molecular sieves / 1) toluene, -20 deg C, 2 h; 2) toluene, -20 deg C, 48 h, then 0 deg C, 75 h
2: 97 percent / NaOMe / methanol / 10 h / Ambient temperature
3: 78 percent / p-toluenesulfonic acid / dimethylformamide / 0.42 h / 60 °C
4: 1) Hg(CN)2 / 1) CH2Cl2, 2 h; 2) CH2Cl2, room temp., 30 h
5: NaOMe / CH2Cl2; methanol / 1 h / Ambient temperature
6: p-TsOH / dimethylformamide / 0.5 h / Ambient temperature
7: pyridine / 5 h / Ambient temperature
8: aq. acetic acid / 0.08 h / Ambient temperature
9: 1) Hg(CN)2, HgBr2 / 1) CH2Cl2, 2 h; 2) CH2Cl2, room temp., 21 h
10: H2S, Et3N / 1) pyridine, H2O, room temp., 12 h; 2) pyridine, 0 deg C, 6 h
With
molecular sieve; silver silicate; hydrogen sulfide; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; triethylamine; mercury dibromide;
In
pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(87)80100-3