Technology Process of 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether
There total 10 articles about 4-azido-2,3,5,6-tetrafluorobenzyl 6-((2R)-6-{[tert-butyl-dimethyl-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl)-hexyl ether which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
6-((2R)-6-{[tert-butyl(dimethyl)-silyl]-oxy}-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-yl)-1-hexanol;
With
potassium tert-butylate;
In
tetrahydrofuran;
at 0 ℃;
for 0.666667h;
4-azido-4-(bromomethyl)-2,3,5,6-tetrafluorobenzene;
In
tetrahydrofuran;
at 0 - 20 ℃;
Further stages.;
DOI:10.1021/jo000029l
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: LiHMDS / tetrahydrofuran / 1 h / 20 °C
1.2: 86 percent / tetrahydrofuran / 3 h / 20 °C
2.1: 100 percent / H2 / Pd/C / ethyl acetate / 18 h
3.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 0 °C
3.2: 69 percent / tetrahydrofuran / 0 - 20 °C
With
potassium tert-butylate; hydrogen; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; ethyl acetate;
1.1: deprotonation / 1.2: Wittig reaction / 2.1: Hydrogenolysis / 3.1: deprotonation / 3.2: Alkylation;
DOI:10.1021/jo000029l
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 97 percent / imidazole / dimethylformamide / 5 h / 85 °C
2.1: 86 percent / DIBAL-H / hexane / 2.5 h / -57 °C
3.1: LiHMDS / tetrahydrofuran / 1 h / 20 °C
3.2: 86 percent / tetrahydrofuran / 3 h / 20 °C
4.1: 100 percent / H2 / Pd/C / ethyl acetate / 18 h
5.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 0 °C
5.2: 69 percent / tetrahydrofuran / 0 - 20 °C
With
1H-imidazole; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide;
1.1: silylation / 2.1: Reduction / 3.1: deprotonation / 3.2: Wittig reaction / 4.1: Hydrogenolysis / 5.1: deprotonation / 5.2: Alkylation;
DOI:10.1021/jo000029l
