Lithium borohydride → HCID 21866249, Verbindung

HRID 857789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857789
Cl[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[CH3:14])=[N:5][S:4][N:3]=1.[BH4-].[Li+]>C1COCC1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[CH:2]=[N:3][S:4][N:5]=2)=[C:8]([CH3:14])[CH:9]=1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 21866306HCID 21866306, Verbindung

Produkt 1

HCID 21866249HCID 21866249, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 3-chloro-4-(4-chloro-2-methylphenyl)-1,2,5-thiadiazole (0.503 g, 2.05 mmol) in THF (5.0 mL) was added 2 M lithium borohydride in THF (2.05 mL, 4.10 mmol). The reaction was stirred at ambient temperature for 15 min then was quenched with water and extracted into EtOAc. The organic phase was dried (Na2SO4) and reduced in vacuo. The residue was purified by flash chromatography (eluting with CH2Cl2/hexanes gradient, 1–15% CH2Cl2). 3-(4-Chloro-2-methylphenyl)-1,2,5-thiadiazole was isolated as a solid. 1H NMR (CDCl3, 400 MHz) δ 2.49 (s, 3H), 7.30 (d, J=8.2 Hz, 2H), 7.34 (s, 1H), 7.53 (d, J=8.2 Hz, 1H), 8.71 (s, 1H); MS m/z=211.4.

Aufarbeitung

  1. customthen was quenched with water
  2. extractionextracted into EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customThe residue was purified by flash chromatography (eluting with CH2Cl2/hexanes gradient, 1–15% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-8361b420cddc4db6adfe733272c77706
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144899B2

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