Tetravinylstannane → 2-Chloro-6-(hydroxymethyl)-4-vinylpyridin-3-ol

HRID 965849

Reaktionsgleichung

Reaktionsgleichung von HRID 965849
[Cl:1][C:2]1[C:7]([OH:8])=[C:6](I)[CH:5]=[C:4]([CH2:10][OH:11])[N:3]=1.[CH:12]([Sn](C=C)(C=C)C=C)=[CH2:13]>CN(C=O)C.CCOC(C)=O.[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>[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([CH:12]=[CH2:13])[CH:5]=[C:4]([CH2:10][OH:11])[N:3]=1

Komponenten

6

Edukt 2

HCID 66189TetravinylstannaneHCID 106845682-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol

Produkt 1

HCID 223132782-Chloro-6-(hydroxymethyl)-4-vinylpyridin-3-olAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-Chloro-6-(hydroxymethyl)-4-iodopyridin-3-ol (5.7 g, 20 mmol) is combined with bis (triphenylphosphine) palladium dichloride (1.12 g, 1.6 mmol) in 50 ml DMF under nitrogen. The mixture is treated with tetravinyl tin, is warmed to 60° C. for 6 h followed by 50° C. for 18 h, and at rt for 72 h. The mixture is diluted with 250 ml EtOAc and is extracted with 4×100 ml 2:1:1 water/saturated NaCl/saturated NaHCO3. The organic layer is dried (MgSO4) and is concentrated in vacuo to a yellow oil. The crude material is chromatographed over 200 g SiO2 (230-400 mesh) eluting with 37% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 1.45 g (39%) of 2-chloro-6-(hydroxymethyl)-4-vinylpyridin-3-ol as a pale yellow solid. MS for C8H8ClNO2 (EI) m/z: 185 (M)+.

Aufarbeitung

  1. waitat rt for 72 h
  2. extractionis extracted with 4×100 ml 2:1:1 water/saturated NaCl/saturated NaHCO3
  3. dry with materialThe organic layer is dried (MgSO4)
  4. concentrationis concentrated in vacuo to a yellow oil
  5. customThe crude material is chromatographed over 200 g SiO2 (230-400 mesh)
  6. washeluting with 37% EtOAc/hexane
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-67e925bc1bd74458935cc949ce28af44
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951868B2

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