2-Propyn-1-ol, 3-(trimethylsilyl)- → [3-(2,6-Dichloro-phenyl)-3H-[1,2,3]triazol-4-yl]-methanol

HRID 424778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424778
[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:11])=[N+:2]=[N-:3].C[Si](C)(C)[C:14]#[C:15][CH2:16][OH:17]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:4]=1[N:1]1[C:15]([CH2:16][OH:17])=[CH:14][N:3]=[N:2]1

Komponenten

5

Edukt 2

HCID 789302-Propyn-1-ol, 3-(trimethylsilyl)-HCID 116008082-Azido-1,3-dichloro-benzene

Produkt 1

HCID 66704184[3-(2,6-Dichloro-phenyl)-3H-[1,2,3]triazol-4-yl]-methanolAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-azido-1,3-dichloro-benzene (4.00 g, 1 equiv) and 3-trimethylsilanyl-prop-2-yn-1-ol (6.29 mL, 2 equiv) in toluene (10 mL) is heated to 120° C. for 23 h. The reaction mixture is allowed to cool to room temperature and is diluted with 100 mL methylene chloride. The solution is adsorbed onto diatomaceous earth and is purified via flash chromatography eluting with hexanes/ethyl acetate (85:15 to 20:80) to give [3-(2,6-Dichloro-phenyl)-3H-[1,2,3]triazol-4-yl]-methanol (2.30 g, 44%) as an off-white solid.

Aufarbeitung

  1. customis purified via flash chromatography
  2. washeluting with hexanes/ethyl acetate (85:15 to 20:80)

Quellen und Nachweise

ORD-Eintrag
ord-4a1092523785402cb704fdb4ce39eb38
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106077B2

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