Multi-step reaction with 11 steps
1.1: ammonia / methanol / 24 h / 20 °C
1.2: NaH / dimethylformamide / 12 h / 20 °C
2.1: 18-crown-6 / dioxane / 12 h / Heating
3.1: ammonia / methanol / 12 h / 20 °C
4.1: NaH / tetrahydrofuran / 0.25 h / 20 °C
4.2: tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C
5.1: aq. AcOH / 12 h / 20 °C
6.1: magnesium; iodine / tetrahydrofuran / 1 h / 40 °C
6.2: 71 percent / tetrahydrofuran / 12 h / 20 °C
7.1: pyridinium dichromate; 3 Angstroem molecular sieves / CH2Cl2 / 2 h / 20 °C
8.1: 246 mg / aq. NaBH4 / tetrahydrofuran / 0.5 h / 20 °C
9.1: 88 percent / N,N,N',N'-tetramethylazodicarboxamide; PBu3 / benzene / 12 h / 20 °C
10.1: 52 percent / DDQ; water / CH2Cl2 / 4 h / 20 °C
11.1: 54 percent / pyridine / 12 h / 20 °C
With
pyridine; sodium tetrahydroborate; dipyridinium dichromate; 18-crown-6 ether; tributylphosphine; 3 A molecular sieve; diamide; ammonia; water; iodine; sodium hydride; magnesium; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; benzene;
6.2: Grignard addition / 9.1: Mitsunobu reaction;
DOI:10.1039/b310719a