Water → 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 631907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631907
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][Si](C)(C)C)[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2].O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:18])[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 715002025-(4-bromo-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 712664555-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl esterAusbeute 45,42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 5-(4-bromo-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (1.9 g, 4.974 mmol) in THF (40 mL), was added water (0.18 mL, 9.948 mmol) and cooled to 0° C. Then TBAF (1M) solution in THF (5.9 mL, 5.9 mmol) was added and the mixture was stirred at 0° C. for 10 min. Volatiles were distilled off and crude mass was purified by normal silica gel column chromatography using EtOAc-hexane as eluting solvent to get 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (0.7 g, 45.42% yield) as an off white solid. LC-MS: 310 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.23 (t, J=7.0 Hz, 3H), 4.27 (s, 3H), 4.31 (q, J=7.0 Hz, 2H), 7.68 (s, 4H). The regio-chemistry was confirmed by NOE study.

Aufarbeitung

  1. distillationVolatiles were distilled off
  2. customcrude mass was purified by normal silica gel column chromatography
  3. washas eluting solvent

Quellen und Nachweise

ORD-Eintrag
ord-84bf16375ada4541b12efff75398fb66
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321738B2

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