2,6-Lutidine → (3,5-Dichlorophenoxy)tris(propan-2-YL)silane

HRID 75238

Reaktionsgleichung

Reaktionsgleichung von HRID 75238
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C(C)=CC=CC=1C.O([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[O:9][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 115713,5-DichlorophenolHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

Produkt 1

HCID 21594466(3,5-Dichlorophenoxy)tris(propan-2-YL)silaneAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3,5-dichloro-phenol (5.9 g, 36 mmol) in methylene chloride (50 mL,) was added 2,6-lutidine (8.38 mL, 72.4 mmol) and triisopropylsilyl triflate (9.7 mL, 36 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 4 h. The reaction was quenched with 0.1 N HCl and diluted with ethyl acetate. The organic solution was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified with flash chromatography (5% ethyl acetate/hexanes) to give the desired product as a colorless oil (10.5 g, 91%). 1H NMR (400 MHz, CDCl3): δ 6.95 (t, J=1.8 Hz, 1 H), 6.76 (d, J=1.8 Hz, 2 H), 1.26 (m, 3 H), 1.09 (d, J=7.0 Hz, 18 H).

Aufarbeitung

  1. customThe reaction was quenched with 0.1 N HCl
  2. additiondiluted with ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with flash chromatography (5% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1d1d219f150d49b980fe0b4cfd8300ce
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835423B2

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