Multi-step reaction with 16 steps
1: pyridine
2: boron trifluoride diethyl etherate; triethylamine / dichloromethane / 24 h / 0 - 20 °C / Molecular sieve 4A
3: trimethylsilyl trifluoromethanesulfonate / chloroform-d1 / 26 h
4: sodium methylate / methanol / 16 h / 20 °C / Inert atmosphere
5: CSA / N,N-dimethyl-formamide / 18 h / 20 °C
6: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere
7: pyridinium p-toluenesulfonate / isopropyl alcohol / 72 h / 20 °C / Inert atmosphere
8: pyridine; dmap / 1.5 h / 0 - 20 °C / Inert atmosphere
9: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere
10: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 0 - 20 °C / Molecular sieve 4A; Inert atmosphere
11: 2,6-di-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / dichloromethane / 20 h / 40 °C / Inert atmosphere; Molecular sieve 4A
12: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C
13: pyridine / 1 h / 20 °C
14: sodium methylate / tetrahydrofuran; methanol / 4 h / 0 - 20 °C
15: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
16: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
With
pyridine; 1H-imidazole; dmap; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate;
In
tetrahydrofuran; methanol; chloroform-d1; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/ja208528c