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Trimethylsilylacetylene → HCID 19365967, Verbindung

HRID 850094
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 850094
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16]([C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1
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Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 17892901HCID 17892901, Verbindung

Produkt 1

HCID 19365967HCID 19365967, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-(2,4-difluorophenyl)-3-(4-iodophenyl)-1-(1,2,4-triazol-1-yl)-3-buten-2-ol (7.0 g, 15.5 mmol-see Preparation 20), trimethylsilylacetylene (2.6 ml, 18.5 mmol), cuprous iodide (0.015 g, 0.15 mmol), bis(triphenylphosphine) palladium (II) dichloride (0.21 g, 0.3 mmol) and triethylamine (80 ml) was stirred at room temperature under a nitrogen atmosphere for 24 hours. Volatile materials were removed under reduced pressure and the residue was partitioned between dichloromethane (200 ml) and a solution of ethylenediaminetetraacetic acid (2 g) in water (100 ml). The organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was chromatographed on silica by elution with dichloromethanelmethanol (95:5). Fractions containing the desired product were combined and evaporated under reduced pressure to give 2-(2,4-difluorophenyl)-3-(4-[trimethylsilylethynyl]phenyl)-1-(1,2,4-triazol-1-yl)-3-buten-2-ol (6.4 g, 98%) as a yellow foam which was characterised by 1H-N.M.R. spectroscopy, (300 MHz, CDCl3): δ=0.22 (s,9H), 4.57 (d,1H), 4.89 (d,1H), 5.16 (s,1H), 5.26 (d,2H), 6.60-6.80 (m,2H), 7.21 (d,2H), 7.38 (d,2H), 7.42 (m,1H), 7.80 (s,2H) ppm.

Aufarbeitung

  1. customVolatile materials were removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane (200 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe crude product was chromatographed on silica by elution with dichloromethanelmethanol (95:5)
  6. additionFractions containing the desired product
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-236364b6b9e849b69c2edad08f4d3577
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06015825

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