Sodium hydride → tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamate

HRID 474278

Reaktionsgleichung

Reaktionsgleichung von HRID 474278
[H-].[Na+].[C:3]([O:7][C:8](=[O:15])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])([CH3:6])([CH3:5])[CH3:4].F[C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[N:26]1[CH:30]=[N:29][C:28]([CH3:31])=[N:27]1>C1COCC1>[CH3:31][C:28]1[N:29]=[CH:30][N:26]([C:18]2[CH:17]=[CH:22][C:21]([N+:23]([O-:25])=[O:24])=[CH:20][C:19]=2[O:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8](=[O:15])[O:7][C:3]([CH3:6])([CH3:4])[CH3:5])[N:27]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamateHCID 575269631-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

Produkt 1

HCID 66666004tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamateAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (0.405 g, 10.13 mmol) was suspended in THF (6 mL), and then tert-butyl-(4-hydroxybutyl)carbamate (1.278 g, 6.75 mmol) in THF (6.0 mL) was added. The reaction mixture was stirred at 0° C. for 10 min, followed by the addition of 1-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (1.0 g, 4.50 mmol) in THF (10.0 mL). The mixture was stirred at 0° C. for 1 h and then stirred for an additional 2 h at rt. The reaction was quenched with water and extracted with EtOAc three times. After concentrating the combined EtOAc layers, the residue was purified by flash chromatography (silica gel, 300 g, 0 to 80% EtOAc/Hexane) to get tert-butyl (4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butyl)carbamate (1.75 g, 99% yield). LC-MS (M+Na)+=414.5. 1H NMR (500 MHz, chloroform-d) δ 8.88 (s, 1H), 8.10 (d, J=8.8 Hz, 1H), 8.00 (dd, J=8.9, 2.3 Hz, 1H), 7.95 (d, J=2.3 Hz, 1H), 4.28 (t, J=6.5 Hz, 2H), 3.22 (d, J=6.4 Hz, 2H), 2.52 (s, 3H), 2.01-1.92 (m, 2H), 1.74-1.68 (m, 2H), 1.46 (s, 9H).

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. stirringstirred for an additional 2 h at rt
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc three times
  5. concentrationAfter concentrating the combined EtOAc layers
  6. customthe residue was purified by flash chromatography (silica gel, 300 g, 0 to 80% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6b08aa0f3d744230b084b5631f29c42d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637523B2

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