Aluminium lithium hydride → 1-(4-fluorobenzyl)-4-(5-(hydroxymethyl)-4-methylthiazol-2-yl)-1H-1,2,4-triazol-5(4H)-one

HRID 1882399

Reaktionsgleichung

Reaktionsgleichung von HRID 1882399
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19](OCC)=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([CH2:19][OH:20])=[C:16]([CH3:18])[N:17]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 57919964ethyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate

Produkt 1

HCID 579199041-(4-fluorobenzyl)-4-(5-(hydroxymethyl)-4-methylthiazol-2-yl)-1H-1,2,4-triazol-5(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate (2.26 g, 6.23 mmol) in anhydrous tetrahydrofuran (60.0 mL) was added lithium aluminium hydride (0.35 g, 9.33 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 4 h, then quenched with 10% aqueous hydrochloric acid solution (3 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was triturated with ether to the title compound: mp 164-166° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.64 (s, 1H), 7.30 (dd, J=8.7, 8.7 Hz, 2H), 7.15 (dd, J=8.7, 8.7 Hz, 2H), 4.96 (s, 2H), 4.57 (s, 2H), 2.22 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.7, 160.5, 150.2 (d, 3JC-F=12 Hz), 143.2, 132.8 (d, 3JC-F=11 Hz), 132.5, 130.7, 130.4 (d, 3JC-F=33 Hz), 116.9 (d, 3JC-F=86 Hz), 55.3, 48.1, 15.1; MS (ES+) m/z 321.2 (M+1).

Aufarbeitung

  1. customquenched with 10% aqueous hydrochloric acid solution (3 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with ether to the title compound

Quellen und Nachweise

ORD-Eintrag
ord-ee963080f70f45e4be41c9cec25e13e5
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318949B2

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